(-)-QUINIC ACID IN ORGANIC-SYNTHESIS .4. SYNTHESES OF CYCLOPHELLITOL AND ITS (1R,6S)-DIASTEREOISOMER, (2S)-DIASTEREOISOMER, (1R,2S,6S)-DIASTEREOISOMER

被引：39

作者：

SHING, TKM

TAI, VWF

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 14期

关键词：

D O I：

10.1039/p19940002017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclophellitol 1 and its (1R,6S)-,(2S)-, (1R,2S,6S)-diastereoisomers 2, 3 and 4 are constructed from quinic acid involving the following key steps: regioselective cyclic sulfate ring opening, regiospecific oxidative elimination and an epoxidation. Diastereoisomers 1, 2, 3 and 4 are characterized as their corresponding tetraacetates 5, 6, 7 and 8.

引用

收藏

页码：2017 / 2025

页数：9

相关论文

共 28 条

[1]

AKIYAMA T, 1991, SYNLETT, P831

[2] PRODUCTION, ISOLATION AND STRUCTURE DETERMINATION OF A NOVEL BETA-GLUCOSIDASE INHIBITOR, CYCLOPHELLITOL, FROM PHELLINUS SP [J].

ATSUMI, S ;

UMEZAWA, K ;

IINUMA, H ;

NAGANAWA, H ;

NAKAMURA, H ;

IITAKA, Y ;

TAKEUCHI, T .

JOURNAL OF ANTIBIOTICS, 1990, 43 (01) :49-53

[3] BIOLOGICAL-ACTIVITIES OF CYCLOPHELLITOL [J].

ATSUMI, S ;

IINUMA, H ;

NOSAKA, C ;

UMEZAWA, K .

JOURNAL OF ANTIBIOTICS, 1990, 43 (12) :1579-1585

[4]

BUCHANAN JG, 1973, ORGANIC CHEM 1, V7, P33

[5] ALKYLATION OF THE CYCLIC SULFAMATE OF PROLINOL - PREPARATION OF OPTICALLY-ACTIVE 2-ALKYL-SUBSTITUTED PYRROLIDINES [J].

COOPER, GF ;

MCCARTHY, KE ;

MARTIN, MG .

TETRAHEDRON LETTERS, 1992, 33 (40) :5895-5896

[6] STUDIES RELATED TO CYCLOPENTANOID NATURAL-PRODUCTS .2. AN IMPROVED ROUTE TO (4R)-4-HYDROXY-2-HYDROXYMETHYLCYCLOPENT-2-EN-1-ONE AND ITS O-SUBSTITUTED DERIVATIVES [J].

ELLIOTT, JD ;

KELSON, AB ;

PURCELL, N ;

STOODLEY, RJ ;

PALFREYMAN, MN .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10) :2441-2449

[7] VICINAL DIOL CYCLIC SULFATES - LIKE EPOXIDES ONLY MORE REACTIVE [J].

GAO, Y ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7538-7539

[8] ASPECTS OF STEREOCHEMISTRY .1. STEREOSPECIFICITY IN FORMATION OF EPOXIDES FROM CYCLIC ALLYLIC ALCOHOLS [J].

HENBEST, HB ;

WILSON, RAL .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (MAY) :1958-1965

[9]

JOHNSON BM, 1990, SYNLETT, P209

[10] CYCLIC SULFATES CONTAINING ACID-SENSITIVE GROUPS AND CHEMOSELECTIVE HYDROLYSIS OF SULFATE ESTERS [J].

KIM, BM ;

SHARPLESS, KB .

TETRAHEDRON LETTERS, 1989, 30 (06) :655-658