A formal total synthesis of eleutherobin through an unprecedented kinetically controlled ring-closing-metathesis reaction of a densely functionalized diene

被引：50

作者：

Castoldi, D

Caggiano, L

Panigada, L

Sharon, O

Costa, AM

Gennari, C

机构：

[1] Univ Milan, ISTM, CNR, Dipartimento Chim Organ & Ind,Ctr Eccellenza CISI, I-20133 Milan, Italy

[2] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 04期

关键词：

antitumor agents; asymmetric synthesis; metathesis; natural products; total synthesis;

D O I：

10.1002/anie.200461767

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The key step in a formal total synthesis of eleutherobin was an unprecedented kinetically controlled RCM reaction of a densely functionalized diene 1 bearing two PMP-protected allylic alcohols in the presence of a second-generation Grubbs catalyst. Subsequent isomerization of the E 10-membered enedione 2 to the more stable 2 isomer and cleavage of the MOM protecting group led to the known precursor 3. MOM = methoxymethyl; PMP = p-methoxyphenyl.

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收藏

页码：588 / 591

页数：4

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