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ISSN 0300-922X JCPRB4(13) 1555-1744(1992) JOURNAL OF THE CHEMICAL SOCIETY Perkin Transactions I Organic and Bio-organic Chemistry CONTENTS Perkin Communications 1555 Mycinamicin biosynthesis: intact incorporation of an intermediate by a chain-elongation process in Micrornonospora griseorubidn Hideaki Suzuki, Satoshi Takenaka, Kenji Kinoshita, Yuji Kogami, Tatsuro Fujiwara and Toshiro Morohoshi 1557 A short synthesis of karahana ether by a radical cyclisation path Toshio Honda, Masayuki Satoh and Yuji Kobayashi 1559 New photochemical cyclisation of 9-(6-anilinohexyl)phenanthrene Akira Sugimoto, Ryoichi Hiraoka, Hiroo Inoue and Tomohiro Adachi 1561 Selective reduction of carboxylic acids with zinc borohydride in the presence of trifluoroacetic anhydride Brindaban C.Ranu and Asish R. Das 1563 Regiospecific deuteriation of chiral 3-isopropyl-2,5-dimethoxy-3,6-dihydropyrazinesin the stereospecific synthesis of x-deuteriated x-amino acids Janet E. Rose, Paul D. Leeson and David Gani Artides 1569 Polyfluoroalkylation of octa-177-diene promoted by dichlorobis(n-cyclopentadieny1)titanium and iron powder Chang-Ming Hu and Yao-Ling Qiu 1573 C-Nucleoside studies. Part 23. New and more direct synthesis of 3-(~-~-xylofuranosyl)pyrazoleJ. Grant Buchanan, M. Luisa Quijano and Richard H. Wightman 1577 Olivanic acid analogues. Part 11. Ozonolysis of x-ethylideneazetidinones: ozonide fragmentation to x-amino acid-N- carboxyanhydrides John H. Bateson, Stephen C. M. Fell, Arun C. Kaura and Robert Southgate 1583 Reactions of 19-ethoxycarbonyl-19-demethylvincadifformine:synthesis of 19-ethoxycarbonyl- 19-demethylapo- vincamine Abdelhamid Belattar and J.Edwin Saxton 1587 A simple approach to the bicyclo5.3.lundecane system present in taxanes Goutam Saha, Atashi Karpha, Supti Saha Roy and Subrata Ghosh 1593 Synthesis and reactions of some new heterocyclic bismuth-(In) and -(v) compounds. 5,10-Dihydrodibenzob,ebismine and related systems Hitomi Suzuki, Toshihiro Murafuji and Nagao Azuma 1601 Oxidation of 1,lO-phenanthroline by tetraoxomanganate(v1) and (VII). Preparation, structure and properties of 1H-cyclopenta2,1 -b :3,4-brsquo;dipyridine-2,5-dione Paul N. W. Baxter, Joseph A. Connor, John D. Wallis, David C. Povey and Anne K. Powell 1607 Chemi- and bio-luminescence of coelenterazine analogues with phenyl homologues at the C-2 position Chen Feng Qi, Yasushiro Gomi, Takashi Hirano, Mamoru Ohashi, Yoshihiro Ohmiya and Frederick I.Tsuji 1613 Synthesis of 1,2-dihydroisoquinoline-3-carbaldehydes Gyula Simig 161 7 Some unexpected reactions involving diphenylketene Rakesh Maurya, Carlos A. Pittol, Robert J. Pryce, Stanley M. Roberts, Russell J. Thomas and Julian 0.Williams 1 CONTENTS 1623 Synthesis of dendritic polyamides uia a convergent growth approach Kathryn E. Uhrich and Jean M. J. FrCchet 1631 Water-promoted organic synthesis using glyco-organic substrates: the Claisen rearrangement AndrC Lubineau, Jacques AugC, Nathalie Bellanger and Sylvie Caillebourdin 1637 Stereocontrolled synthesis of (2S,3S,8S,9S,4E,6E)-3-amino-9-methoxy-2,6,8-trimethyl-lO-phenyldeca-4,6-dienoicacid (Adda), the amino acid characteristic of microcystins and nodularin Mark F.Beatty, Clive Jennings-White and Mitchell A. Avery 1643 Synthesis of selectively multi-labelled histidines with stable isotopes and chiral synthesis of L-histidine from L-aspartic acid Takashi Furuta, Motofusa Katayama, Hiromi Shibasaki and Yasuji Kasuya 1649 Biosynthetic studies on the chitinase inhibitor, allosamidin. Origin of the carbon and nitrogen atoms Ze-Yang Zhou, Shohei Sakuda and Yasuhiro Yamada 1653 Chemoenzymatic approach to the synthesis of the antiviral agents penciclovir and famciclovir in isotopically chiral rsquo;3C labelled form John T. Sirne, Roger D. Barnes, Stephen W.EIson, Richard L. Jarvest and Kevin J. Orsquo;Toole 1659 Reaction of diphenyl disulfide with alkynes promoted by di-tert-butyl and dibenzoyl peroxide: a useful synthetic route to 3-(and 2,3-) substituted benzobthiophenes Luisa Benati, Pier Carlo Montevecchi and Piero Spagnolo 1665 P-Stereospecific hydroboration of 13-epi-pimar-8( 14)-enes Arturo San Feliciano, Manuel Medarde, Esther Caballero, Fernando Tomb and BelCn Hebrero 1671 Synthesis of isothiocyanato-1- 1-(2-benzohthienyl)cyclohexylpiperidines, potential irreversible ligands at the dopamine re-uptake site Brian de Costa, Clifford George and Celia Dorninguez 1681 The absolute stereochemistries of ( +)-toddalolactone and its related chiral coumarins from Todddia usiatica (L.) Lam.( T. ucufeata Pers.) and their optical purities Hisashi Ishii, Jun-Ichi Kobayashi, Eri Sakurada and Tsutomu Ishikawa 1685 Mechanism and stereochemistry of the enzyme-catalysed formation of a 2,2-dimethylchromene ring from a prenylated phenol: conversion of rot-2rsquo;-enonic acid into deguelin by deguelin cyclase Prabha Bhandari, Leslie Crombie, Mark F. Harper, John T. Rossiter, Mark Sanders and Donald A. Whiting 1699 Solid-phase synthesis and characterization of 0-dimannosylated heptadecapeptide analogues of human insulin-like growth factor 1 (IGF-1) Anita M. Jansson, Morten Meldal and Klaus Bock 1 709 Reactions of diene-conjugated 1,3-dipolar intermediates: the formation of cyclopropacisoquinolines from benzonitrile o-alkenylbenzyl ylides and their rearrangements to benzazepines Keith R.Motion, Ian R. Robertson, John T. Sharp and Malcolm D. Walkinshaw I721 Synthesis and stereochemistry of an optically active selenonium ylide. X-ray molecular structure of (+)se-{4rsquo;-(-)-menthyloxycarbonylphenyl)(methyl)selenonium 4,4-dimethyl-2,6-dioxocyclohexylideNobumasa Kamigata, Yoshihiro Nakamura, Koichi Kikuchi, Isao Ikemoto, Toshio Shimizu and Haruo Matsuyama 1729 Synthesis of 2-alkenylpyrazol-3(2H)-one derivatives under mild conditions Graziano Baccolini, Daniele Evangelisti, Corrado Rizzoli and Paolo Sgarabotto 1735 Epoxidation and Baeyer-Villiger oxidation of y-hydroxy-+unsaturated ketones on exposure to m-chloroperbenzoic acid Marioara Mendelovici and Erwin Glotter 1741 Conference Diary AUTHOR INDEX Adachi, Tomohiro, 1559 Auge, Jacques, 163 1 Avery.Mitchell A., 1637 Azuma, Nagao, 1593 Baccolini, Grdziano, 1729 Barnes, Roger D., 1653 Bateson. John H., 1577 Baxter, Paul N. W., 1601 Beatty. Mark F., 1637 Belattar, Abdelhamid. 1583 Bellanger, Nathalie, 163 1 Benati, Luisa, 1659 Bhandari, Prabha. 1685 Bock, Klaus, 1699 Buchanan, J. Grant, 1573 Caballero, Esther, 1665 Caillebourdin, Sylvie, 163 1 Connor, Joseph A., 1601 Crombie, Leslie, 1685 Das. Asish R .. I56 1 de Costa. Brian, 1671 Dominguez. Celia, 167 1 Elson. Stephen W., 1653 Evangelisti, Daniele, I729 Fell, Stephen C. M., 1577 Frechet, Jean M. J., 1623 Fujiwara, Tatsuro, 1555 Furuta, Takashi, 1643 Gani, David.1563 George, Clifford, 167 1 Ghosh, Subrata, 1587 Glotter, Erwin, 1735 Gomi, Yasushiro, 1607 Harper, Mark F., 1685 Hebrero, BelCn, 1665 Hirano, Takashi, 1607 Hiraoka, Ryoichi, 1559 Honda, Toshio, 1557 Hu, Chang-Ming, 1569 Ikemoto, Isao, 172 1 Inoue, Hiroo, 1559 Ishii, Hisashi, 168 1 Ishikawa, Tsutomu, 1681 Jansson, Anita M., 1699 Jarvest, Richard L., 1653 Jennings-White, Clive, 1637 Kamigata, Nobumasa, 172 1 Karpha, Atashi, 1587 Kasuya, Yasuji, I643 Katayama. Motofusa, 1643 Kaura, Arun C., 1577 Kikuchi, Koichi, 172 1 Kinoshita, Kenji, 1555 Kobayashi, Jun-Ichi, 168 1 Kobayashi, Yuji, 1557 Kogami, Yuji, 1555 Leeson, Paul D., 1563 Lubineau, Andre, 163 1 Matsuyama, Haruo, 1721 Maurya, Rakesh, 161 7 Medarde, Manuel, 1665 Meldal, Morten, 1699 Mendelovici, Marioara, 1735 Montevecchi, Pier Carlo, 1659 Morohoshi, Toshiro, 1555 Motion, Keith R., 1709 Murafuji, Toshihiro, 1593 Nakamura, Yoshihiro, 1721 Ohashi, Mamoru, 1607 Ohmiya, Yoshihiro, 1607 Orsquo;Toole, Kevin J., 1653 Pittol, Carlos A., 1617 Povey, David C., 1601 Powell, Anne K., 1601 Pryce, Robert J., 1617 Qi, Chen Feng, 1607 Qiu, Yao-Ling, 1569 Quijano, M.Luisa, 1573 Ranu, Brindaban C., 1561 Rizzoli, Corrado, 1729 Roberts, Stanley M., 1617 Robertson, Ian R., 1709 Rose, Janet E., 1563 Rossiter, John T., 1685 Roy, Supti Saha, 1587 Saha, Goutam, 1587 Sakuda, Shohei, 1649 Sakurada. Eri, 1681 San Feliciano, Arturo, 1665 Sanders, Mark, 1685 Satoh, Masayuki, 1557 Saxton, J. Edwin, 1583 Sgarabotto, Paolo, 1729 Sharp, John T., 1709 Shibasaki, Hiromi, 1643 Shimizu, Toshio, 1721 Sime, John T., I653 Simig, Gyula, 161 3 Southgate, Robert, 1577 Spagnolo, Piero, 1659 Sugimoto, Akira, 1559 Suzuki, Hideaki, 1555 Suzuki, Hitomi, 1593 Takenaka, Satoshi, 1555 Thomas, Russell J., 16 17 Tome, Fernando, 1665 Tsuji, Frederick I., 1607 Uhrich, Kathryn E., 1623 Walkinshaw, Malcolm D., 1709 Wallis, John D., 1601 Whiting, Donald A., 1685 Wightman, Richard H., 1573 Williams, Julian O., 16 17 Yamada, Yasuhiro, 1649 Zhou, Ze-Yang. 1649 NOTE: An asterisk in the heading of each paper indicates the author who is to receive any correspondence. ... 111