ISSN 0300-922X JCPRB4(11) 1201-1274(1993) JOURNAL OF THE CHEMICAL SOCIETY Perkin Transactions I Organic and Bio-organic Chemistry CONTENTS Perkin Communications 120 1 Preparation of 6-0~0-1,6-dihydropyridine-2-carboxylic acid by microbial hydroxylation of pyridine-2-carboxylic acid Qy" 0 H O Andreas Kiener, Rainer Glockler and Klaus Heinzmann The bacterium Alcaligenesfaecalis (DSM 6269) has been used for the regiospecific hydroxylation of pyridine-2-carboxylic acid to 6-0x0-1,6-dihydropyridine-2-carboxylicacid on a preparative scale 1203 Do metal perchlorates act as a conventional Lewis acid in the allylstannation of aldehydes? Metal perchlorates (M = Li, Mg, Ca) in ether are found to Y utaka Nishigaichi, Noriko Nakano and promote the above reaction via a six-membered cyclic transition Akio Takuwa state, not acting as a conventional Lewis acid 1205 Mechanistic pathways for radical ring expansion/aromatisation of steroid C/Dmodels Stuart P.Green and Donald A. Whiting 1 CONTENTS Artides 1207 Pentenyl mannosides in the synthesis of N-acylmannopyranosyl amides: conformational analysis of intermediates C. Srinivas Rao, Andrew J. Ratcliffe and Bert Fraser-Reid 12 13 Preparation of [ 4R-3H] NADH, [ 4R-3H]-NADPH and the corresponding 4s-isomers all with substantial specific activities Koji Ichinose, Finian J. Leeper and Alan R. Bat tersby 1217 Alternative synthesis of q3-methoxybenzy1)- pyrazin-2( 1H)-one. Synthesis of indeno[ 1,241-pyrazin-2-ones. Crystal structures of 5-acetoxy- 1-benzyl4tert-butoxycarbonyl-6-(3-methoxy-benzy1idene)piper azin-2-one, 1-benzyl4tert-butoxycarbony l-7-methox y-1,3,4,4a-tetrahydro-indeno[ 1,241 pyrazin-2-one and 1-benzyl4 tert-butoxycarbonyl-7-methoxy-l,3,4,9-tetrahydro-indeno[ 1,241 pyrazin-2-one David A.Peters, Roy L. Beddoes and John A. Joule 1225 Selectivity and specificity in substrate binding to proteases: novel hydrolytic reactions catalysed by a-chymotrypsin suspended in organic solvents with low water content and mediated by ammonium hydrogen carbonate Jean-Marc Ricca and David H. G. Crout 1235 A practical synthesis of the anti-tumour agent 2-methyl4deoxyisopicropodophyllotoxinand related podophyllin analogues Andrew R. Beard, Sarah J.Hazell, John Mann and Christopher Palmer X'NCORIOPent (;:If R = Aryl or CH&H(NHZ)C0fin I I .MF .MT A cheap and simple enzymic procedure is described for the preparation of both NADH and NADPH tritium-labelled at C-4 with either the R or the S configuration starting with sodium borotritiide Sih3 CONTENTS ~~~ 1239 Synthesis, bioactivation and anti-HIV activity of the bis(4-acyloxybenzyl) and mono(4-acyl- oxybenzyl) esters of the 5'-monophosphate of AZT William Thomson, Dave Nicholls, William J. Irwin, Julian S. Al-Mushadani, Sally Freeman, Abraham Karpas, Juraj Petrik, Naheed Mahmood and Alan J. Hay 1247 Isolation, structural elucidation and conformational analysis of sesquiterpene pyridine alkaloids from Maytenus ebenifolia Reiss.X-Ray molecular structure of ebenifoline W-I Hideji Itokawa, Osamu Shirota, Hiroshi Morita, Koichi Takeya and Yoichi Iitaka 1255 Chiral polyhydroxylated tetrahydrothiophene derivatives: novel synthesis and structural elucidation by X-ray crystallography, NMR spectroscopy and molecular mechanics calculations A. V. Rama Rao, K. Ashok Reddy, N. R. Srinivas, M. K. Gurjar, N. Padmaja, S. Ramakumar, M. A. Viswamitra, G. V. T. Swapna, B. Jagannadh and A. C. Kunwar I26 1 The elimination of an alkoxy group in the photo-Graebe-Ullmann conversion of 142,sdialkoxypheny1)triazolopyridines into carbolines, and the preparation of a-,y-and karboline quinones Lina K. Mehta, John Parrick and Fereshteh Payne 1269 Synthesis of the oligosaccharide segment of a novel phenolic glycolipid antigen from MycobacteriumAaemophihm M.K. Gurjar and K. Revathi Reddy 0 0 II II (~-RCO&~H~CH~~)ZP 4-FCO&&l4CHfl-Y-AZl--AzT 0-6 7 Designed to improve membrane penetration, the biolabile prodrugs, 5 and 7give the 5'-monophosphate of AZT in the presence of porcine liver carboxyesterase The conformation of ebenifolines and o the flexibility of their macrocyclic ring systems have been elucidated The syntheses and structures of novel polyhydroxylated tetrahydrothiophene derivatives obtained from Barton-McCombie reactions of 1,3,4,6-di-O-alkylidene-2,5-di-S-methylthiocarbonyl-~-mannitol derivatives are described X =CH or N whenY IN or CH/k/FT R Md W -dkow Dialkoxycarbolines yield carboline quinones on oxidation with CAN The synthesis of the trisaccharide: 2,3-di-O-Me-~-Rhap-(a I 2)-3--P 0-Me-L-Rhap(al +4)-2,3-di-O-Me-~-Rhap-(al+ isolated from Mycobacterium haemophilum phenolic glycolipid is described ...111 CONTENTS Corrigenda 1273 New congeners of swinholides from the okinawan marine sponge Theoneflusp. Sachiko Tsukamoto, Masami Ishibashi, Takuma Sasaki and Jun'ichi Kobayashi 1 273 Phosphorus-based reagents in peptide synthesis: synthesis of methionine-enkephalin and the solution conformation of its Ndiphenylphosphinyl derivative D. David Smith, David Hopton, Kenneth G. Boyd, Robert L. Baxter and Robert Ramage vii Conference Diary iv AUTHOR INDEX Al-Mushadani, Julian S., 1239 Battersby, Alan R., 1213 Baxter.Robert L., 1273 Beard, Andrew R., 1235 Beddoes. Roy L., 1217 Boyd. Kenneth G., 1273 Crout, David H. G., 1225 Fraser-Reid, Bert, 1207 Freeman. Sally, 1239 Glockler. Rainer, 1201 Green, Stuart P., 1205 Gurjar, M. K., 1255, 1269 Hay, Alan J., 1239 Hazell, Sarah J., 1235 Heinzmann. Klaus, 1201 Hopton, David, 1273 Ichinose, Koji, 121 3 litaka, Yoichi, 1247 Irwin, William J., 1239 Ishibashi, Masami, 1273 Itokawa, Hideji, 1247 Jagannadh, B., 1255 Joule, John A., 1217 Karpas, Abraham, 1239 Kiener, Andreas, I201 Kobayashi, Jun’ichi, 12’73 Kunwar, A. C., 1255 Leeper, Finian J., 1213 Mahmood, Naheed, 1239 Mann, John, 1235 Mehta, Lina K., 1269 Morita, Hiroshi, 1247 Nakano, Noriko, 1203 Nicholls, Dave, 1239 Nishigaichi, Yutaka, 1203 Padmaja, N., 1255 Palmer, Christopher, 1235 Parrick, John, 1269 Payne, Fereshteh, I261 Peters, David A., 12 17 Petrik, Juraj, 1239 Ramage, Robert, 1273 Ramakumar, S., 1255 Rao, A.V. Rama, 1255 Rao, C. Srinivas, 1207 Ratcliffe, Andrew J., 1207 Reddy, K. Ashok, 1255 Reddy, K. Revathi, 1269 Ricca, Jean-Marc, 1225 Sasaki, Takuma, 1273 Shirota, Osamu, 1247 Smith, D. David, 1273 Srinivas, N. R., 1255 Swapna, G. V. T., 1255 Takeya, Koichi, 1247 Takuwa, Akio, 1203 Thomson, William, 1239 Tsukamoto, Sachiko, 1273 Viswamitra, M. A., 1255 Whiting, Donald A., 1205 NOTE: An asterisk in the heading of each paper indicates the author who is to receive any correspondence. V
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