Total synthesis of dolatrienoic acid: A subunit of dolastatin 14

被引：29

作者：

Moune, S ^{[1
]}

Niel, G ^{[1
]}

Busquet, M ^{[1
]}

Eggleston, I ^{[1
]}

Jouin, P ^{[1
]}

机构：

[1] UPR 9023,F-34094 MONTPELLIER 5,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 10期

关键词：

D O I：

10.1021/jo962217a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The (7R,15R)- and (7S,15R)-diastereomers of dolatrienoic acid were synthesized using a convergent strategy. Fragment C5-C9 was obtained through enantiodifferentiation of racemic pentane-1,3,5-triol as the key step, fixing the chirality at C7 of fragments 4 and ent-4. The chirality at C15 of the fragment C10-C16 was introduced from L-glutamic acid. Coupling of these two fragments led to the aldehydes (7R,15R)- and (7S,15R)-2 which were homologated by Horner-Wadsworth-Emmons condensation to give (7R,15R)- and (7S,15R)-dolatrienoic acids.

引用

页码：3332 / 3339

页数：8

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