STUDIES IN TERPENOID BIOSYNTHESIS .39. THE STEREOCHEMISTRY OF THE RELATIONSHIP BETWEEN SUBSTRATE AND OXIDANT IN THE HYDROXYLATION OF APHIDICOLIN AT C-18 BY CEPHALOSPORIUM-APHIDICOLA

被引：8

作者：

HANSON, JR ^{[1
]}

HITCHCOCK, PB ^{[1
]}

JARVIS, AG ^{[1
]}

RATCLIFFE, AH ^{[1
]}

机构：

[1] ICI PLC, MACCLESFIELD SK10 4TG, CHESHIRE, ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 16期

关键词：

D O I：

10.1039/p19920002079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of some 3-alpha,18-oxetane analogues of intermediates in the biosynthesis of aphidicolin is described. Their stereoselective labelling at C-18 with deuterium is reported. Biotransformation studies using these substrates with Cephalosporium aphidicola have shown that the 18-pro-R-hydrogen is removed in hydroxylation at this centre suggesting a Re stereochemical relationship between the substrate and oxidant for the normal hydroxylation at C-18. The X-ray crystallographic structure of 3-alpha,18-oxetane 6 is presented and compared with that of aphidicolin 17-nor-16-ketone 13.

引用

页码：2079 / 2085

页数：7

共 3 条

[1] STUDIES IN TERPENOID BIOSYNTHESIS .37. AN O-18 STUDY OF THE BIOSYNTHESIS OF THE DITERPENOID, APHIDICOLIN IN CEPHALOSPORIUM-APHIDICOLA
ACKLAND, MJ
GORDON, J
HANSON, JR
YEOH, BL
RATCLIFFE, AH
[J]. PHYTOCHEMISTRY, 1988, 27 (04) : 1031 - 1033
[2] STUDIES IN TERPENOID BIOSYNTHESIS .35. BIOSYNTHETIC SEQUENCES LEADING TO THE DITERPENOID APHIDICOLIN IN CEPHALOSPORIUM-APHIDICOLA
ACKLAND, MJ
GORDON, JF
HANSON, JR
YEOH, BL
RATCLIFFE, AH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (06): : 1477 - 1480
[3] STUDIES IN TERPENOID BIOSYNTHESIS .32. THE INCORPORATION OF APHIDICOL-16-ENE AND APHIDICOLAN-16-BETA-OL INTO THE DITERPENOID APHIDICOLIN BY THE FUNGUS CEPHALOSPORIUM-APHIDICOLA
ACKLAND, MJ
HANSON, JR
YEOH, BL
RATCLIFFE, AH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12): : 2705 - 2707

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