STUDIES DIRECTED TOWARDS THE TOTAL SYNTHESIS OF ANTICAPSIN AND RELATED-COMPOUNDS .3. A RING-FRAGMENTATION ROUTE TO THE ANTICAPSIN SKELETON

被引：5

作者：

CROSSLEY, MJ

STAMFORD, AW

机构：

[1] School of Chemistry, University of Sydney

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1994年 / 47卷 / 09期

关键词：

D O I：

10.1071/CH9941713

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The alpha-amino-5-oxo-7-oxabicyclo[4.1.0]heptane-2-propanoic acid framework of anticapsin and related compounds is generated by base-catalysed fragmentation of 2-amino-5,6-epoxy-1-hydroxybicyclo[2.2.2]octane-2-carboxylic acid derivatives in a retro-aldol-like reaction.

引用

页码：1713 / 1726

页数：14

共 14 条

[1] STEREOCONTROLLED ENANTIOSPECIFIC SYNTHESIS OF ANTICAPSIN - REVISION OF THE CONFIGURATION
BALDWIN, JE
ADLINGTON, RM
MITCHELL, MB
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[2] BRIGDEN KM, UNPUB
[3] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES
COREY, EJ
VENKATESWARLU, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) : 6190 - +
[4] CONCISE, STEREOCONTROLLED SYNTHESIS OF THE C4 EPIMERS OF ANTICAPSIN AND BACILYSIN - REVISION OF THE CONFIGURATIONS OF THE NATURAL-PRODUCTS
CROSSLEY, MJ
STAMFORD, AW
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1993, 46 (09) : 1443 - 1446
[5] STUDIES DIRECTED TOWARDS THE TOTAL SYNTHESIS OF ANTICAPSIN AND RELATED-COMPOUNDS .2. DIELS-ALDER ADDITION OF N-ACYL DEHYDROALANINE ESTERS TO 1-TRIMETHYLSILYLOXYCYCLOHEXA-1,3-DIENE
CROSSLEY, MJ
STAMFORD, AW
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (09) : 1695 - 1711
[6] STUDIES DIRECTED TOWARDS THE TOTAL SYNTHESIS OF ANTICAPSIN - X-RAY CRYSTAL-STRUCTURE OF (1RS,2SR,4RS,5RS,6SR)-5-HYDROXY-2-PHTHALIMIDO-1-TRIMETHYLSILYLOXY-BICYCLO[2.2.2]OCTANE-2,6-CARBOLACTONE
CROSSLEY, MJ
HAMBLEY, TW
STAMFORD, AW
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (11) : 1827 - 1837
[7] CROSSLEY ML, UNPUB
[8] CLEAVAGE OF T-BUTYLDIMETHYLSILYL ETHERS WITH BORON-TRIFLUORIDE ETHERATE
KELLY, DR
ROBERTS, SM
NEWTON, RF
[J]. SYNTHETIC COMMUNICATIONS, 1979, 9 (04) : 295 - 299
[9] NEW CROSS-ALDOL REACTIONS - REACTIONS OF SILYL ENOL ETHERS WITH CARBONYL-COMPOUNDS ACTIVATED BY TITANIUM TETRACHLORIDE
MUKAIYAMA, T
BANNO, K
NARASAKA, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (24) : 7503 - 7509
[10] STRUCTURE OF ANTICAPSIN, A NEW BIOLOGICALLY ACTIVE METABOLITE OF STREPTOMYCES-GRISEOPLANUS
NEUSS, N
MOLLOY, BB
SHAH, R
DELAHIGUERA, N
[J]. BIOCHEMICAL JOURNAL, 1970, 118 (04) : 571 - +

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