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ISSN 0300-922X JCPRB4(21) 3053-3256(1994) JOURNAL OF THE CHEMICAL SOCIETY Perkin Transactions I Organic and Bio-organic Chemistry CONTENTS Perkin Communications NHR33053 A new and efficient synthesis of cytidine and S adenosine derivatives by dimethyldioxirane 0-0oxidation of thiopyrimidine and thiopurine nucleosides 'K AcO Raffaele Saladino, Claudia Crestini, OAc R2 R3= alkyl or aryl OAc R2Roberta Bernini, Giuseppe Frachey and Enrico Mincione R2=HorOH R1=HorMe 3055 Biosynthesis of astellatol, a novel rearranged sester ter penoid met a boli te of Aspergillusvariecolor 1 Incorporation of 1,2-' 3C,acetate into asteiiatol I confirms its Thomas J. Simpson biosynthesis via geranylfarnesyl pyrophosphate Ph 3057 Exploration for large-scale stereoselective synthesis of unusual amino acids by using 4-phen yloxazolidinone as a new chiral resolution reagent Ph.NH2Me 0 0 'n---Ph4k32H Guigen Li, Dinesh Pate1 and Victor J. Hruby Me 0 0 the Four isomers 306 1 Synthesis of the phosphonate isostere of carbocyclic 5-bromovinyldeoxyuridinemonophosphate Diane M. Coe, Antonio Garofalo, Stanley M. Roberts, Richard Storer and Andrew J. Thorpe 1 CONTENTS Articles 3065 Synthesis and trapping of 4H- and 5H-thieno3,4-c pyrroles Chin-Kang Sha and Chiu-Peng Tsou 3071 Intermediatesfor the synthesis of linear chains of 1,2 :4,5-fused cyclohexa-1,4-diene rings and beltenes by repeated Diels-Alder reactions Roger W. Alder, Paul R. Allen, Lee S. Edwards, Gordon I.Fray, Katy E. Fuller, Paul M. Gore, Nicholas M. Hext, Martin H. Perry, Alex R. Thomas and Kevin S. Turner 3079 The stereochemical course of decarboxylation,transamination and elimination reactions catalysed by Escherichiu culi glutamic acid decar box ylase Kevin Tilley, Mahmoud Akhtar and David Gani 3089 Mechanisms and stereochemistry of the activation of (2s)-and (2R)-serine 0-sulfate as suicide inhibitors for Escherichiu culi glutamic acid decarboxylase Janet E. Rose, Paul D. Leeson and David Gani Mexs02 + =* Me OR I OAc I 0 OR I (R = SiMe2Bu') OR OAc OR Active pyridoxal -HI3 phosphate-+$kwm;kecid -glutamicacid decarboxylase 2-03m* hobenzyme Me H 3 The stereochemical courses of the a-decarboxylation of (2s)-aspartic acid and the abortive transamination decarboxylation of the coenzyme with (2S)-glutamic acid as substrate are also described -02amp; -HASO,-Inactive ___) 0 -enzyme*O,PO complex H H (2s)-Inhibitor-PLP aldimlne The inactivation of the enzyme by the (2R)-enantiomer also occurs but follows a different mechanism 11 CONTENTS 3095 Boron halide catalysed regioselective ovtho-Claisen rearrangements of 4'-allylox ycoumaricacid derivatives: total synthesis of demethylsuberosin Nicholas Cairns, Laurence M.Harwood, David P. Astles and Alex Orr 3101 Tandem thermal Claisen-Cope rearrangements of coumarate derivatives. Total syntheses of the naturally occurring coumarins: suberosin, demethylsuberosin, ostruthin, balsamiferone and gravelliferone Nicholas Cairns, Laurence M.Harwood and David P. Astles 3109 Formal synthesis of the juglomycins Margaret A. Brimble and Elaine Ireland 3 115 Reactions involving fluoride ion. Part 38. New fluorinated dienes by defluorination Mark W. Briscoe, Richard D. Chambers, Steven J. Mullins, Takayuki Nakamura, Julian F. S. Vaughan and Frederick G. Drakesmith 3119 Reactions involving fluoride ion. Part 39. Reactions of perfluorinated dienes with oxygen and sulphur nucleophiles Mark W. Briscoe, Richard D. Chambers, Steven J. Mullins, Takayuki Nakamura and Julian F. S. Vaughan 3125 Catalytic asymmetric synthesis of y-hydroxyketones and aromatic hydroxy ketones by the chemo- and enantio-selective alkylation of keto aldehydes with dialkylzincs Masami Watanabe and Kenso Soai R' 6-Substituted coumarins are prepared via regioselective Lewis acid catalysed rearrangements of methyl 4'-allyloxycoumarates R3 R3AR4 e.g. R' , R5 = H or prenyl 6-Substituted and 3,6-disubstituted coumarins are prepared oia multiple 3,3)sigmatropic rearrangements of methyl 2'-all ylox ycoumarates Me0 OH Me0 0 0 H' OH + R22Zn Chiralcatalyst~ 0 OH iii CONTENTS 3 129 Polar cycloaddition of 2-benzothiopyrylium salts with conjugated dienes Hiroshi Shimizu, Shojiro Miyazaki, Tadashi Kataoka, Mikio Hori and Osamu Muraoka 3141 Photocatalysed addition of alcohols to 5-substituted 2,5-dihydrofuran-2-ones:novel synthesis of (3'R)-2',3'dideoxy- 3'-hydroxymethyl nucleosides John Mann and Alexander C.Weymouth-Wilson 3 149 Asymmetric induction in the electrocyclisation reactions of 1,3dipolar intermediates: the 1.7 cyclisation of diene-conjugated diazo- compounds to give 1H-2,3-benzodiazepines Alexander J. Blake, Mervyn Harding and John T. Sharp 3 163 The phosphorylation of organic compounds by phosphoric anhydride. Part 3. Synthesis of monosubstituted ketenes in the reaction of esters with phosphoric anhydride and cyclotrimerization of these ketenes Dimitry A. Efremov, Pave1 M. Zavlin, Nataly S. Essentseva and John C. Tebby 3169 Carbonyl phosphonylation via 1N,3E-bifunctional reagents. Probing mechanistic and reactivity features through chemical and isotopic labelling Paul G.Devitt and Terence P. Kee 3183 1N,3E-Bifunctional phosphorodiamidites and the diastereoselective phosphonylation of aldehydes. Controlling, elucidating and rationalising the stereochemical course of the asymmetric Abramov reaction Vivienne Sum, Christopher A. Baird, Terence P. Kee and Mark Thornton-Pett BF4-1 2 2-Benzothiopyrylium salts 1 undergo a polar cycloaddition with conjugated dienes to afford benzo-fused bicyclic sulfonium salts 2 having sulfur at a bridgehead position in good yields HO-' Face selectivity is strongly influenced by the nature of the medium sized group R3 I px' H i, p4deg;10Z-CH2-C02R 'c=c=o -ii, H2O Z/ z 2 1 3 Monosubstituted ketenes 1have been synthesized from substituted acetic esters 2 by elimination of alcohol under the action of phosphoric anhydride; the ketenes undergo cyclotrimerisation to give substituted 1,3,5-trihydroxybenzenes3 and their phosphorylated derivatives 0 (R3 = Ph3Bu'Me2, Et3) (R'= Ph; R3 = Ph3, BdMe,, Et3) (R'= Bu'; R3 = Ph3, Bu'Me2, Et3) N SiMe3 iv CONTENTS 3201 Amino acids and peptides.Part 38. Development of a new amino-protectinggroup,2-adamantyloxycarbonyl,and its application to peptide synthesis Yasuhiro Nishiyama, Noriyuki Shintomi, Yukihiro Kondo and Yoshio Okada 3209 Reaction of 3-(acetoxyamino)quinazolin-4(3H)-ones with enolic p-diketones: the N-N bond as a chiral axis in N-(3,4dihydro4oxoquinazolin-3-yl)-N-acyl-a-aminoketon;reductive and base-catalysed cleavage of the N-N bond in N-acetyl-N-(3,4dihydro4oxoquinazolin-3-yl)-a-amino acid esters Robert S.Atkinson, Paul J. Edwards and Gordon A. Thomson 3217 Synthesis based on cyclohexadienes. Part 15. Total synthesisof (3)-prezizaene, 3-prezizanol and ( k Fjinkohol I1 Natesan Selvakumar and G. S. R Subba Rao 3225 Studies on the structure of the sesquiterpenecaespitenoneisolated from Porella species of liverwort Motoo Tori, Yoshihiro Kohama, KatsuyukiNakashima and Yoshinori Asakawa 3231 A convenient enantioselectivesynthesisof (+)-8-epi-g oniofu fur one Zhi-Cai Yang and Wei-shan Zhou i. cu** c ii. 2-AdoeCI iii. EOTA A new amp;-aminoprotecting group, 2-adamantyloxycarbonyl(2-Adoc), has been developed, and its application to the solid-phase synthesisof protected peptides in combination with N"-Fmoc protection and TFA-cleavable solid support as well as the solution-phase peptide synthesisdependingon Boc-chemistry are described NHoAc 8 11 14n5 14/15 Exist as stable diastereoisomersbecause the Q-N bond is a chiral axis 12 10 6 norprezizanone pnkohol I1 0 I oamp; 0, 1 20 The structure of caespitenone isolated from the liverwort Porella caespitans var.setigera or P. swartziana has been revised from 1to 20 including the absolute configurationby 2D NMR techniques and syntheticstudies CONTENTS 3233 Chemistry and occurrence of taxane derivatives. Part 16. Rearranged taxoids from Taxus x media Rehd.cv Hicksii. X-Ray molecular structure of 9-0-benzoyl-9,lOdide- 0-acetyl-1 l(15 --+ 1)abeo-baccatin VI Luciano Barboni, Pierluigi Gariboldi, Elisa be t t a Torregiani, Giovanni Appendino, Giancarlo Cravotto, Ezio Bombardelli, Bruno Gabetta and Davide Viterbo 3239 Photoinduced molecular transformations. Part 149. Stereospecific photoadditions and photorearrangementsof the oximes of some steroidal a,fl-unsaturated cyclic ketones and their deuterio derivatives Hiroshi Suginome, Koji Ohshima, Yoshihiko Ohue, Takashi Ohki and Hisanori Senboku 3251 Natural product chemistry. Part 181. Investigations on the synthesis of dihydropyrano- and dihydrofurano-coumarins by application of catalytic enantioselective cis-dihydroxyla t ion Johannes Reisch and Arnd A.W. Voerste ix Conference Diary AcO-2 3 Rrsquo;=R4=H, R2=R3=Ac 4 Rrsquo;=Ac. R2=Bz, R3=R4=H 5 Rrsquo;=R3=Ac, Rrsquo;=BZ, R4=H The new 1 1(1 5 -1)abeo-taxanes2-5 have been isolated from the roots of Taxus x media Rehd. cv Hicksii 0 at the ring jundon HO ldquo;OH (rear-side attack) __c Hrsquo; MeOD amp;Me The c=c bond (front-sideattadc)at the nonringjunchion OH 1b (-)-amp;(lS, 2s) 4 IC (-)-rrans(i s, 2~) AUTHOR INDEX Akhtar, Mahmoud, 3079 Alder, Roger W., 3071 Allen, Paul R., 3071 Appendino, Giovanni, 3233 Asakawa, Yoshinori, 3225 Astles, David P., 3095, 3101 Atkinson, Robert S., 3209 Baird, Christopher A., 3183 Barboni, Luciano, 3233 Bernini, Roberta, 3053 Blake, Alexander J., 3149 Bombardelli, Ezio, 3233 Brimble, Margaret A,, 3109 Briscoe, Mark W., 31 15, 31 19 Cairns, Nicholas, 3095, 3 101 Chambers, Richard D., 31 15, 31 I9 Coe, Diane M., 3061 Cravotto, Giancarlo, 3233 Crestini, Claudia, 3053 Devitt, Paul G., 3169 Drakesmith, Frederick G., 31 15 Edwards, Lee S., 3071 Edwards, Paul J., 3209 Efremov, Dimitry A., 3163 Essentseva, Nataly S., 3163 Frachey, Giuseppe, 3053 Fray, Gordon I., 307 1 Fuller, Katy E., 3071 Gabetta, Bruno, 3233 Gani, David, 3079,3089 Gariboldi, Pierluigi, 3233 Garofalo, Actonio, 3061 Gore, Paul M., 3071 Harding, Mervyn, 3149 Harwood, Laurence M., 3095, 3101 Hext, Nicholas M., 3071 Hori, Mikio, 3129 Hruby, Victor J., 3057 Ireland, Elaine, 3 109 Kataoka, Tadashi, 3 129 Kee, Terence P., 3 169, 3 183 Kohama, Yoshihiro, 3225 Kondo, Yukihiro, 3201 Leeson, Paul D., 3089 Li, Guigen, 3057 Mann, John, 3 141 Mincione, Enrico, 3053 Miyazaki, Shojiro, 3 129 Mullins, Steven J., 3115, 3119 Muraoka, Osamu, 3 129 Nakamura, Takayuki, 3 115, 31 19 Nakashima, Katsuyuki, 3225 Nishiyama, Yasuhiro, 3201 Ohki, Takashi, 3239 Ohshima, Koji, 3239 Ohue, Yoshihiko, 3239 Okada, Yoshio, 3201 Orr, Alex, 3095 Patel, Dinesh, 3057 Perry, Martin H., 3071 Reisch, Johannes, 325 1 Roberts, Stanley M., 3061 Rose, Janet E., 3089 Saladino, Raffaele, 3053 Selvakumar, Natesan, 3217 Senboku, Hisanori, 3239 Sha, Chin-Kang, 3065 Sharp, John T., 3149 Shimizu, Hiroshi, 3 129 Shintomi, Noriyuki, 3201 Simpson, Thomas J., 3055 Soai, Kenso, 3125 Storer, Richard, 3061 Subba Rao, G.S. R., 3217 Suginome, Hiroshi, 3239 Sum, Vivienne, 3183 Tebby, John C., 3163 Thomas, Alex R., 3071 Thomson, Gordon A., 3209 Thornton-Pett, Mark, 3 183 Thorpe, Andrew J., 3061 Tilley, Kevin, 3079 Tori, Motoo, 3225 Torregiani, Elisabetta, 3233 Tsou, Chiu-Peng, 3065 Turner, Kevin S., 3071 Vaughan, Julian F. S., 31 15, 31 19 Viterbo, Davide, 3233 Voerste, Arnd A. W., 3251 Watanabe, Masami, 3 125 Weymouth-Wilson, Alexander C., 3141 Yang, Zhi-Cai, 323 1 Zavlin, Pave1 M., 3163 Zhou, Wei-shan, 323 1 NOTE: An asterisk in the heading of each paper indicates the author who is to receive any correspondence.vii Forthcoming Articles in Perkin Transactions I Reactions of Tetrasulfur Tetranitride with Aryl Dibromomethyl Ketones: One Pot Synthesis of 3-Aroylformamido-4-aryl-1,2,5-thiadiazoles and their Reactions K.Kim, J. Cho and S.C. Yoon Photoresponsive Melittin Having a Spiropyran Residue in the Hydrophobic Region of the Sequence S. Kimura, T. Oeda, K. Nagamine and Y. Imanishi Stereocontrol in the Nucleophilic Epoxidation of a-(1 -Hydrox yaky1)-a$-unsaturated Sulfones R.F.W. Jackson, S.P. Standen, W. Clegg and A. McCamley Control of Diasterofacial Selectivity in the Nucleophilic Epoxidation of y-Oxygenated-a#-unsaturated Sulfones R.F.W. Jackson, S.P. Standen and W. Clegg Effect of Molecular Sieves on the Formation and Acid-catalysed Mono- and Bis-cyclization of N-Arylimines.An Easy Entry to Polycyclic Ring Systems by a Novel Cascade Reaction S. Laschat and 0.Temme Enantiopure Didemnenones via Kinetic Resolution E. Winterfeldt and M. Gores Optical Resolution and Absolute Stereochemistry of truns-2,5-Dimethyl- 1 -phenyl- 1 -silacyclopentane B.P. Roberts, HA. Dang and D.A. Tocher Asymmetric Synthesis of (lR,l'R)-and (lS,1's)-Diaryldiethylamines by way of a Diastereoselective Addition of Chiral Imines and 1,3-Oxazolidines with Organometallic Reagents K. Higashiyama, H. Inoue, T. Yamauchi and H. Takahashi Synthetic Applications of Arenetricarbonylchromium(0) Complexes: The Synthesis of Polyfunctionalised Thiophenes D.A. Widdowson, M.S. Loft and T.J.Mowlem Nickel-catalysed Substitutions of Aryl tert-Butyl Sulfones with Organometallic Reagents: Synthesis of ortho-Substituted Unsymmetrical Biaryls J. Clayden, J.J.A. Cooney and M. Julia PbClJGa Bimetal Redox System-mediated Reactions of Carbon-Carbon Bond Formation between Carbonyl Compounds with Ethyl Trichloroacetate and with Iodoacetonitrile X.-L. Zhang, W.-T. Tao and Y.-2. Huang Oxazolidinofullerene T.-Y. Luh, L.-L. Shiu, K.-M. Chien, T.-Y. Liu, T.-I. Lin, G.-R. Her and S.-L. Eng Regioselectivity in the Reductive Cleavage of Pyrogallol Derivatives: Reductive Electrophilic Substitution of Acetals of 2,3-Dimethoxyphenol U.Azzena, G. Melloni and L. Pisana On the Mechanism of Phototransformations of 3-Alkoxy-2-(2-furyl)-4-oxo-4H-1-benzopyrans S.C.Gupta, A. Saini, D. Kumar, N.S. Yadav, K. Chand, S. Mor and S.N. Dhawan M. Kobayashi Additivity Relationships in the Carbon- 13 Nuclear Magnetic Resonance Spectra of Polyhydroxy Steroids (Halogenomethy1)phenyl a-D-Glucopyranosides as Enzyme Activated Irreversible Inhibitors of Yeast a-Glucosidase and Potential Anti-HIV Agents A.H. Haines, J.C. Briggs and R.J.K. Taylor Radical Cyclisation in Heterocycle Synthesis. Part 1. Thiyl Radical Addition-Cyclisation of Dienylamides for Lactam Synthesis T. Naito, Y.Honda, 0. Miyata and I. Ninomiya Improved Synthesis of Isoguanosine and 6-Substituted Xanthosine Derivatives G. Piccialli, L. de Napoli, D. Montesarchio, C. Santacroce and M. Varra Allene-based Electrophile-mediated Cyclisations: Efficient Synthesis of Medium Ring Azacycles T. Gallagher and R.W. Shaw Synthesis of Medium Ring Azacycles via Allene-based Cyclisations: Evaluation of Possible Mechanistic Pathways T. Gallagher, I.W. Davies, R.W. Shaw and R.Wisedale 5,9-Methanobenzocycloalkenamines.Part 1. An Improved Synthesis of 1 1-Amino-5,9-methanobenzocyclooctenes D.R. Rae, I.M. Gilbert, C.L. Hewett, J. Redpath, D.S. Savage and T.Sleigh