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ISSN 0300-922X JCPRB4(21) 2667-281 O(1995) JOURNAL OF THE CHEMICAL SOCIETY Perkin Transactions I Organic and Bio-organic Chemistry CONTENTS Perkin Communications 2667 Stereoselective synthesis of 3-p~-H ribofuranosylpyrazole from 2,3-0-isopropylidene-D-ribose; a new route to pyrazole C-nucleos ides stereoselective conversion -HmdAnthony D. Rycroft, Gurdial Singh and I1Richard H. Wightman MeOx0Me HO OH 2669 Samarium diiodide promoted coupling of thiophenecarbaldehydes ,CHO *o* OH R Thiophene-2-carbaldehydeor thiophene-3-carbaldehydeadd to Shyh-Ming Yang and Jim-Min Fang aromatic or aliphatic aldehydes with the mediation of Sm1,-HMPA 2673 Enantioselective synthesis of a-arylpropanoicacids Philip C. Bulman Page, Michael J. McKenzie up to 93ee and Derek R.Buckle 2677 Facile synthesis of the key intermediate of EO 9 via the formation of the indole skeleton using the Nenitzescu reaction Masahiko Kinugawa, Hitoshi Arai, Hiroshi Nishikawa, Akihiko Sakaguchi, Takehiro Ogasa, Shinji Tomioka and Masaji Kasai i CONTENTS 2679 Facile retro-cycloaddition of adducts derived from steroidal 5,7-diene and 4-phenyl-l,2,4- triazoline-3,5dione by diisobutylaluminium DIBALHhydride 0 lsquo;C, tdueno ~-RO amp; 51-94 Fumihiro Kondo, Misako Miyashita, Katsuhiro Konno and Hiroaki Takayama 268 1 Preparation and direct observation by I9FNMR spectroscopy of 1-fluoro-1-lithioalkenes LiKF CH2=CFLi Ph2C=CFLi 1 2 3 Andrew Pelter, Jaroslav Kvicala and Ab initio calculations on 1 and 19F NMR spectroscopic studies to David E.Parry establish the half lives of 2 and 3 are given 2683 Novel synthesis of 3-chloromethylidene-2-ethoxy-1,2S5-oxaphospholan-2-ones catalysedby palladium(rr) Chunlin Ma, Xiyan Lu and Yongxiang Ma Art icIes Fh.. @miEd) 2685 lsquo;Activersquo; conformation of the inositol Wlsquo; Adenosine 2rsquo;-phosphate and a range monophosphatase substrate, adenosine 2rsquo;-of analogues have been used to study phosphate: role of the ribofuranosyl 0-atoms the mechanism of inositol monophos- phatase. The 2rsquo;-0 atom and the ribo- in chelating a second Mg2+ ion furanosyl ring 0-atom are involved in interacting with a second catalytic Mg2+ ion at the active site of the enzyme. This second metal ion may position and activate a water molecule for the phosphate ester hydrolysis Andrew G.Cole and David Gani reaction P ~0-H rsquo;+ 2695 Probes for the position and mechanistic role of the second lsquo;catalyticrsquo; magnesium ion in the 15inositol monophosphatase reaction X=O,CH*txJ A range of substrate and inhibitor analogues for inositol monophosphatase have been prepared and used to probe the position of the second catalytic metal ion cofactor; compound 15 appears to prevent phosphate ester hydrolysis by providing a Andrew G. Cole, John Wilkie and hydroxy group that displaccs thc nuclcophilic watcr molecule on David Gani the second Mg2 + ion 11 CONTENTS 2709 $Dimensional interactions between inositol monophosphatase and its substrates, inhibitors and metal ion cofactors John Wilkie, Andrew G.Cole and David Gani 2729 The lithiation of fluorinated benzenes and its dependence on solvent and temperature Paul Leslie Coe, Anthony John Waring and Thomas David Yarwood 2739 Synthesis of 4phenylpiperidines by tandem Wittig olefination-aza-Wittig rearrangement of 2-benzoylaziridines Iain Coldham, Alan J. Collis, Roger J. Mould and Richard E. Rathmell 2747 Synthesis of ( ? )-aklavinone and ( k )-auramycinone via electron-deficient o-quinonoid pyrones David W. Jones and Christopher J. Lock 2757 LICKOR-Promoted 1,2-elimination in 1,l-dimethoxy-2-phenylethaneand 1,ldimethoxy- 2-phenylpropane: synthesis of substituted enol ethers and alkynes Annamaria Deagostino, Mariella Mella, Cristina Prandi and Paolo Venture110 Water The structures of inositol mono- phosphatase complexed with both metal ion cofactors and various sub- strates and inhibitors are presented.The second Mg2 + ion serves to align and activate a water molecule to attack the phosphate P-atom. The structure of an Li + inhibited form of the enzyme that may be impor- tant in the treatment ofmanic depression is also presented F F F (R = H, Br or F, R' = H or Br) -Reagents and conditions: i, LDA, THF, -78 "C; ii, Acetone, -78 OC; iii, BuLi, Et,O, hexane, -78 "C. Autometallation occurs under different conditions Bu'OzC bsol; Ph I 10 2 PWePBr amp;phR room temp. BuLi,DME R H Olefination of 2-benzoylaziridines leads to piperidine products by aza-Wittig rearrangement of the intermediate vinylaziridines generated in situ adducts converted into aklavinone and auramycinone 'wok-R)+ow LICKOR, 1) LICKOR Ph OM3 Ph 2) ,c=o R=H,Me ...111 2761 Regio- and stereo-selective synthesis of trifluoromethylated isoxazolidines by 1,3-diplar cycloaddition of 1,1,l-trifluoro-3-phenylsulfonylpropene with nitrones, and their conversion into trifluoromethylated syn-3-amino alcohols Hiroyasu Tsuge, Takashi Okano and Shoji Eguchi 2767 Synthesis of some analogues of cytisine:unusual reduction pathways for tertiary nitro groups in sterically constrained molecules Kristina J. Blackall, David Hendry, Robert J. Pryce and Stanley M. Roberts 2773 Synthesis of 4-hydroxylamino-l-azabuta-1,3-dienes and their cyclization to 2-substituted pyrazole 1-oxides Jesus Alcazar, Inks Almena, Mikael Begtrup and Antonio de la Hoz 2783 Antitumour imidazotetrazines. Part 33.New syntheses of the antitumour drug temozolomide using 'masked' methyl isocyanates Yongfeng Wang, Malcolm F. G. Stevens,William T. Thomson and Bruce P. Shutts 2789 Ligand coupling and neighbouring-group effects in the alkaline hydrolysis of arylphosphoniumsalts: new stable tetraarylphosphonium benzimidazolate betaines David W. Allen and Peter Benke CONTENTS R2 R=CHorN X = SMe orH t i, Ma-;ii. Hz Raney nickel R R = Me, En, p-Me-Camp;X = H, Br, NO, Y,Z = H, Me Temzolomide (i) Barton radical decarboxylation; (ii) TBAF 2 Hydrolysis of the arylphosphonium salts 1has revealed (a) evidence of neighbouring-group interactions between the azole N and the phosphonium centre in the ortho-isomers and (b) formation of abnormal biaryl coupling products 2 and the stable betaines 3 iv CONTENTS 2795 Synthesis of 1,6-diethynylcyclohepta-l,3,5-triene and its oxidative coupling to dimethano- bridged octadehydro 203 annulene and trimethano-bridged dodecadehydro 301-annulene Jiiro Ojima, Tomoyo Daimon, Naoki Hiraiwa, Hiroyuki Higuchi, Masako Ueno and Gaku Yamamoto 2803 Diastereoselectivity and assignment of absolute stereochemistry in the aza-Diels-Alder reaction of a sulfonylimino acetate with 1-methoxy-3- trimeth ylsilylox ybuta-l,Miene Andrew K.McFarlane, Gareth Thomas and Andrew Whiting Corrigendum 2809 Parasite glycoconjugates.Part 4. Chemical synthesis of disaccharide and phosphorylated oligosaccharide fragments of Leishmania donovani antigenic lipophosphoglycan A. V. Nikolaev, T. J. Rutherford, M. A. J. Ferguson and J. S. Brimacornbe ix Conference Diary V AUTHOR INDEX Alcazar, Jesus, 2773 Allen, David W., 2789 Almena, Ines, 2773 Arai, Hitoshi, 2677 Begtrup, Mikael, 2773 Benke, Peter, 2789 Blackall, Kristina J., 2767 Brimacornbe, J. S., 2809 Buckle, Derek R., 2673 Coe, Paul Leslie, 2729 Coldham, Iain, 2739 Cole, Andrew G., 2685, 2695, Collis, Alan J., 2739 Daimon, Tomoyo, 2795 de la Hoz, Antonio, 2773 Deagostino, Annamaria, 2757 Eguchi, Shoji, 2761 Fang, Jim-Min, 2669 Ferguson, M.A. J., 2809 Gani, David, 2685,2695,2709 Hendry, David, 2767 Higuchi, Hiroyuki, 2795 Hiraiwa, Naoki, 2795 Jones, David W., 2747 Kasai, Masaji, 2677 Kinugawa, Masahiko, 2677 Kondo, Fumihiro, 2679 Konno, Katsuhiro, 2679 Kvicala, Jaroslav, 268 1 Lock, Christopher J., 2747 Lu, Xiyan, 2683 Ma, Chunlin, 2683 Ma, Yongxiang, 2683 McFarlane, Andrew K., 2803 McKenzie, Michael J., 2673 Mella, Mariella, 2757 Miyashita, Misako, 2679 Mould, Roger J., 2739 Nikolaev, A. V., 2809 Nishikawa, Hiroshi, 2677 Ogasa, Takehiro, 2677 Ojima, Jiiro, 2795 Okano, Takashi, 2761 Page, Philip C. Bulman, 2673 Parry, David E., 2681 Pelter, Andrew, 268 1 Prandi, Cristina, 2757 Pryce, Robert J., 2767 Rathmell, Richard E., 2739 Roberts, Stanley M., 2767 Rutherford, T.J., 2809 Rycroft, Anthony D., 2667 Sakaguchi, Akihiko, 2677 Shutts, Bruce P., 2783 Singh, Gurdial, 2667 Stevens, Malcolm F. G., 2783 Takayama, Hiroaki, 2679 Thomas, Gareth, 2803 Thomson, William T., 2783 Tomioka, Shinji, 2677 Tsuge, Hiroyasu, 276 1 Ueno, Masako, 2795 Venturello, Paolo, 2757 Wang, Yongfeng, 2783 Waring, Anthony John, 2729 Whiting, Andrew, 2803 Wightman, Richard H., 2667 Wilkie, John, 2695, 2709 Yamamoto, Gaku, 2795 Yang, Shyh-Ming, 2669 Yarwood, Thomas David, 2729 NOTE: An asterisk in the heading of each paper indicates the author who is to receive any correspondence. vi Forthcoming Articles in Perkin Transactions I Synthesis and stereochemistry of the epoxides of 2-arylidene- 1 -tetralones A.Levai, W. Adam, J. nalasz, 2.Jambor, C. Nemes, T. Patonay and G. Toth Synthesis and characterisation of bis1.lorthocyclophano- 18-crown-6 compounds H. Hara, S. Watanabe and 0. Hoshino Stereocontrolled synthesis of E-homoallylic sulfides with 1,4,5 related chiral centres using the 2,3sigmatropic rearrangement of sulfonium ylides R.C. Hartley, I.C. Richards and S. Warren Novel reductase participating in the syn-addition of hydrogen to the C=C bond of enones in the cultured cells of Nicotiana tabacum K.Shimoda, D.I. Ito, S. Izumi and T. Hirata Highly enantioselective route to rrans-5-substituted-2-hydroxymethylpyrrolidinederivatives by radical cyclisation Y.Yuasa, J. Ando and S. Shibuya Condensed heteroaromatic ring systems. Part 14. Synthesis of rigidin, a pyrrolo2,3-d)pyrimidinemarine alkaloid T. Sakamoto, Y. Kondo, S. Sat0 and H. Yamanaka Synthesis of 1-amino-2,3,4,14b-tetrahydro-lH-dibenzobdpyrido 1,2-4 1,410xazepine and related compounds D.R. Rae, W.L. Caulfield and S. Gibson Synthesis of C-D-ring analogues of the azasteroid A25822 J.K. Sutherland, A.J. Sutherland and P.J. Crowley Synthesis of the key component for preparation of 6-keto-prostaglandins by the two-component coupling process. Synthesis of 6-keto-prostaglandin El, Ornoprostil and A2-trans-6-keto-prostaglandinEl Y. Kawanaka, N. Ono, Y. Yoshida, S. Okamoto and F. Sat0 Reactions of a-trialkylsilylvinyl carbanions with carboxylic acid derivatives: the relationship between product distribution and substrate reactivity P.G.Taylor, A.R. Bassindale, I. Katampe and P.A. Kyle Stereospecific formation of R-aromatic acyloins by Zymomonas mobilis pyruvate decarboxylase D.H.G. Crout, S. Bornemann, H. Dalton, V. Kren, M. Lobell, G. Dean, N. Thomson and M.M. Turner Synthesis of enantiopure a-deuteriated Boc-L-amino acids U. Ragnarsson and Y. Elemes Enzymatic synthesis of hemithiocellodextrins H. Driguez and V. Moreau Photoinduced skeletal rearrangement of 1,l -diarylspiropentanes Y. Takahashi, H. Ohaku, S. Morishima, T. Suzuki, H. Ikeda and T. Miyashi The potential of sulfimides as chiral acyl anion equivalents P.C. Taylor, G.Smith and T.J. Sparey Enantioselective total synthesis of the di-0-methyl ethers of (-)-agatharesinol, (+)-hinokiresinol and (-)-sugiresinol, characteristic norlignans of Coniferue 0.Muraoka, B. Zheng, N.Fujiwara and G. Tanabe Synthesis of dendri tic polypyridines with ethoxycarbonyl groups as surface functionality G. Chessa and A. Scrivanti Thermolysis and photolysis of 1 -substituted triptycenes. Divergent fragmentation pathways of the triptycyl skeleton H. Tomioka and J. Nakajima Reinvestigation of reactions of thiazolium and benzothiazolium N-phenacylides with electron-deficient acetylenes T. Kataoka, T. Iwamura, M. Kobayashi and H. Shimizu Synthesis of 2-deoxy-a-and -P-D-arabino-hexopyranosylphosphonic acids and related compounds: analogues of early intermediates in the Shikimate pathway R.H.Wightman, N.J. Barnes and M.A. Probert Detection of 2-substituted cyclobutanones as irradiation products of lipid-containing foods: synthesis and applications of cis-and trans-2-(tetradec-5-enyl)cyclobutanonesand 11-(2'-oxocyclobutyl)undecanoic acid D.R. Boyd, L. Hamilton, M.H. Stevenson, I.N. Brannigan, A.B. Treacy, J.T.G. Hamilton, W.C. McRoberts and C.T. Elliott JOURNAL OF THE CHEMICAL SOCIETY Perkin Transactions I COM M UNICAT10NS NORTH AMERICAN AUTHORS Please submit your Perkin Communications and Articles to Professor Tomas Hudlicky North American Associate Editor Department of Chemistry University of Florida PO Box 117200 Gainesville FL 326 11-7200 USA COPIES OF CITED ARTICLES The Royal Society of Chemistry Library can usually supply copies of cited articles.For further details contact: The Library, Royal Society of Chemistry, Burlington House, Piccadilly, London UK WlV OBN. Tel +44(0) 171 437 8656. Fax: +44 (0) 171 287 9798. Telecom Gold 84: BUR210. Electronic Mailbox (Internet) LTBRARY@RSC.ORG If the material is not available from the Societyrsquo;s Library, the staff will be pleased to advise on its availability from other sources. Please note that copies are not available from the RSC at Thomas Graham House, Cambridge.