ISSN 0300-922X JCPRB4(20) 2379-2504(1993) JOURNAL OF THE CHEMICAL SOCIETY Perkin Transactions I Organic and Bio-organic Chemistry CONTENTS Perkin Communications 2379 Synthesis and biological activity of =‘co&¶+--“..% stereochemically locked derivatives of jasmonic 0 PrS’acid /+ Jane L. Ward and Michael H. Beale 2383 Arylation of 4-ethoxycarbonyl-2-phenyloxazol-5-one by aryllead triacetates: a convenient route to a-arylglycines Mark J. Koen, Jacqueline Morgan and John T. Pinhey 2385 Dicyanomethylenethiiranesfrom thioketenes and tetracyanoethylene oxide Gunadi Adiwidjaja, Oliver Bolte, Bettina Dietz and Ernst Schaumann 2387 A novel approach to functionalised plycyclic systems; intramolecular DielsAlder reactions of 2-acylated derivatives of 4H,6H=thieno-[3,4-c Jfuran 5,Mioxide 1 2 3 The title compound 1 was converted into 2, which readily cyclised Takaaki Hayashi, Yoh Kawakami, to give stereoselectively the functionalised tricyclic compound 3 in Katsuhiro Kono and Hiroaki Takayama good yield 1 CONTENTS 2389 Polymerisation of 10-hydroxydecanoic acid with the lipase from Cundidu cyfindruceu David O'Hagan and Naveed A.Zaidi 239 1 1,SDipolar cycloadditions of 43-dihydroimidazolium ylides: new protocols for the synthesis of pyrrolidines and pyrrolo- [1,2-u]pyrazines Raymond C. F. Jones and Kevin J. Howard Articles 2395 Intramolecular Diels-Alder reactions of vinylfurans leading to furanodecalins Philip Cornwall, Colin P. Dell and David W.Knight 2407 Enzymatic acylation in the resolution of methyl threo-2-hydroxy-3-(4-methoxyphenyl)-S(2-X-pheny1thio)propionates in organic solvents Liisa T. Kanerva and Oskari Sundholm 2411 Unexpected formation of triarylbismuthdiformates in the oxidation of triarylbismuthines with ozone at low temperatures Hitomi Suzuki, Tohru Ikegami, Yoshihiro Matano and Nagao Azuma The above polyester (a,,9346) has been prepared by condensation polymerisation of the monomer with the CC lipase in hexane ~ Y CH?Ph , 0"'QdR0,d HexahydropyrroloC 1,2-a]imidazoles, formed as cycloadducts from 4,5-dihydroimidazolium ylides via a new simplified protocol give, on reduction, hexahydropyrroloC 1,Za]pyrazines or N-substituted pyrrolidines depending on the nature of the ester 2-Furyl- and 3-furyl-nonadienoates undergo intramolecular Diels- Alder cylisations when heated to 290 "C; (2)-dienes undergo stereospecific reactions whereas the corresponding (E)-isomers show little stereocontrol Compound 3 has been resolved by lipase PS-catalysed acylation Ar3Bi(OCH0)2 1 + AraBi(OAc), 11 a 2417 Radical decarboxylative alkylation onto hetero- aromatic bases with trivalent iodine compounds 0 R-C-OH 00 II It R-OH-R-0-C-C-OH Ar = Ph.X = MeC02, Ar -Ph, X = CF3C02, Ar = CeFs. X = CF3CO2.Hideo Togo, Masahiko Aoki, Tadashi R = 1'. 2". P-dkyland sugar moiety Kuramochi and Masataka Yokoyama 2429 Novel, regioselective allylamine construction; first synthesis of geranyllinaloisocyanide,a diterpene from the marine sponge, Halichondria sp.0 Me Yoshiyasu Ichikawa, Masatugu Yamazaki and Minoru Isobe 2433 A study of the ferrous ion-initiated S,1 reactions of halogenoarenes with tert-butyl R' acetate and N-acylmorpholine enolates X O-Nd + R'CH=L--Y -Fez+ DCHCOY R x-&.I R' = H, alkyl Y IOBd,N(CH2CH2)S Milco van Leeuwen and Alexander McKillop 2441 Donor-acceptor accelerated norbornadiene rearrangements Christine Bleasdale and David W. Jones H2453 Synthesis of optically active amides from NH2 fury1 and p-phenyl esters by way of enzymatic amino1ysis Vicente Gotor, Emma MenCndez, Zephirin Mouloungui and Antoine Gaset 2457 Complexation and photoinduced electron- transfer reaction between perfluoroalkyl iodides and N,N,ICP,N-tetramethylphenylene-l,4-diamine, anilines and piperazines Qing-Yun Chen, Zhan-Ting Li and Irradiation of anilines and RJ in DMF affords the corresponding Cheng-Min Zhou perfluoroalkylated compounds in good yields ...111 2463 An expeditious synthesis of 3-alkyl-, aryl- and heteroaryl-indoles by way of an intramolecular Horner-Wittig reaction Axel Couture, Eric Deniau, Yves Gimbert and Pierre Grandclaudon 2467 Oligomeric flavanoids. Part 16. Novel prorobinetinidins and the first A-type proanthocyanidin with a 5-deoxy A-and a 3,4-cis C-ring from the maiden investigation of commercial wattle bark extract Annemarie Cronje, Jan P. Steynberg,E. Vincent Brandt, Desmond A. Young and Daneel Ferreira 2479 Reaction of 4-phenylbut-3-en-2-one with cyanoacetamide in 2 :1ratio Conor N.O'Callaghan, T. Brian H. McMurry, Christine J. Cardin and Deborah J. Wilcock 2487 A facile one-step synthesis of aromatic indolizines by 1,Mipolar cycloaddition of pyridinium and related heteroaromatic ylides with alkenes in the presence of TPCD [CoPY,(HCrO,)*l Xudong Wei, Yuefei Hu, Tingsheng Li and Hongwen Hu 2491 Copper(n)-catalyzed molecular rearrangements: the behaviour of arylhydrazonesof some 3-benzoylazoles in the presence of copper(I1) acetate Silvestre Buscemi, Vincenzo Frenna, Nicolb Vivona and Domenico Spinelli 2495 Optically active tricarbonyl($-u- trimethylsilylbenzaldehyde)chromium(o)complexes in organic synthesis: a highly diastereoselective 1,3dipolar cycloaddition with electron-rich olefins Chisato Mukai, In Jong Kim, Won Jea Cho, Masaru Kid0 and Miyoji Hanaoka vii Conference Diary CONTENTS A variety of 3-alkyl-, aryl- and heteroaryl-indole derivatives have been efficiently prepared by base-induced intramolecular cyclization of suitable aromatic o-acyl substituted Horner-Wittig reagents The first A-type proanthocyanidin HO with a 5-deoxy A- and a 3,413s OH C-ring is accompanied in commercial wattle bark extract by a range of 'phlobatannins' exhibiting the typical structural features that are essential for the use of 'Mimosa' extract in cold setting adhesives and leather tanning applications OH 2PhCH=CHCOMe 53-93% A facile and general one-step method is presented for the synthesis of the aromatic indolizine compounds 321-n in moderate to high yields (53-9973 by 1,3-dipolar cycloaddition of pyridinium and related heteroaromatic ylides with alkenes in the presence of TPCD CCoPYdHCrO4)J Ph H ArA=N.CH Copper(I1) acetate in methanol effectively induces rearrangement of arylhydrazones of some 3-beazoylazoles (1,2,4-oxadiazole and isoxazole) into the corresponding 1,2,3-triazoles (-)-form iv a Adiwidjaja, Gunadi, 2385 Aoki, Masahiko, 241 7 Azuma, Nagao, 241 1 Beale, Michael H., 2379 Bleasdale, Christine, 2441 Bolte, Oliver, 2385 Brandt, E.Vincent, 2467 Buscemi, Silvestre, 249 1 Cardin, Christine J., 2479 Chen, Qing-Yun, 2457 Cho, Won Jea, 2495 Cornwall, Philip, 2395 Couture, Axel, 2463 Cronje, Annemarie, 2467 Dell, Colin P., 2395 Deniau, Eric, 2463 Dietz, Bettina, 2385 Ferreira, Daneel, 2467 Frenna, Vincenzo, 249 1 Gaset, Antoine, 2453 Gimbert, Yves, 2463 Gotor, Vicente, 2453 Grandclaudon, Pierre, 2463 Hanaoka, Miyoji, 2495 Hayashi, Takaaki, 2387 Howard, Kevin J., 2391 Hu, Hongwen, 2487 Hu, Yuefei, 2487 Ichikawa, Yoshiyasu, 2429 Ikegami, Tohru, 241 1 Isobe, Minoru, 2429 Jones, David W., 2441 Jones, Raymond C.F., 2391 Kanerva, Liisa T., 2407 Kawakami, Yoh, 2387 Kido, Masaru, 2495 Kim, In Jong, 2495 Knight, David W., 2395 Koen, Mark J., 2383 Kono, Katsuhiro, 2387 Kuramochi, Tadashi, 2417 Li, Tingsheng, 2487 Li, Zhan-Ting, 2457 Matano, Yoshihiro, 241 1 McKillop, Alexander, 2433 McMurry, T.Brian H., 2479 Menbndez, Emma, 2453 Morgan, Jacqueline, 2383 Mouloungui, Zephirin, 2453 Mukai, Chisato, 2495 OCallaghan, Conor N., 2479 O'Hagan, David, 2389 Pinhey, John T., 2383 Schaumann, Ernst, 2385 Spinelli, Domenico, 2491 Steynberg, Jan P., 2467 Sundholm, Oskari, 2407 Suzuki, Hitomi, 241 1 Takayama, Hiroaki, 2387 Togo, Hideo, 24 17 van Leeuwen, Milco, 2433 Vivona, Nicole, 2491 Ward, Jane L., 2379 Wei, Xudong, 2487 Wilcock, Deborah J., 2479 Yamazaki, Masatugu, 2429 Yokoyama, Masataka, 2417 Young, Desmond A., 2467 Zaidi, Naveed A., 2389 Zhou, Cheng-Min, 2457 NOTE: An asterisk in the heading of each paper indicates the author who is to receive any correspondence. 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