Applications of crotyldiisopinocampheylboranes in synthesis: a formal total synthesis of (+)-calyculin A

被引：31

作者：

Anderson, OP

Barrett, AGM ^{[1
]}

Edmunds, JJ

Hachiya, SI

Hendrix, JA

Horita, K

Malecha, JW

Parkinson, CJ

VanSickle, A

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

[3] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 2001年 / 79卷 / 11期

关键词：

calyculin; marine natural product; phosphatase inhibitor; total synthesis; palladium catalyzed coupling reactions; allylboration reactions; aldol reactions; spiroketal; Cornforth-Meyers oxazole reaction;

D O I：

10.1139/cjc-79-11-1562

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth-Meyers approach to the synthesis of the oxazole fragment.

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页码：1562 / 1592

页数：31

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