Total synthesis of mycalamide A and 7-epi-mycalamide A

被引：43

作者：

Roush, WR ^{[1
]}

Pfeifer, LA ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 06期

关键词：

D O I：

10.1021/ol005629l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The final stages of a total synthesis of mycalamide A are described. A key step is the aldol reaction (mismatched) of imide 4 and aldehyde 5 which provided a ca. 5:4 mixture of aldols 10a and 10b, with incorrect C(7) stereochemistry, Elaboration of the 10a-10b mixture to mycalamide A required epimerization of C(7) at the stage of beta-keto imide 11. Alternatively, Swern oxidation of the 10a-10b mixture under conditions that minimize C(7) epimerization led to 7-epi-mycalamide A selectively.

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页码：859 / 862

页数：4

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