Total synthesis of bryostatin 2

被引：240

作者：

Evans, DA ^{[1
]}

Carter, PH ^{[1
]}

Carreira, EM ^{[1
]}

Charette, AB ^{[1
]}

Prunet, JA ^{[1
]}

Lautens, M ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1999年 / 121卷 / 33期

关键词：

D O I：

10.1021/ja990860j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of the marine macrolide bryostatin 2 is described. The synthesis plan relies on aldol and directed reduction steps in order to construct the anti-1,3-diol array present in each of the principal subunits (A, B, and C). These fragments were coupled using a Julia olefination and subsequent sulfone alkylation. A series of functionalization reactions provided a bryopyran seco acid, which was macrolactonized under Yamaguchi conditions. Installation of the two enoate moieties took advantage of asymmetric phosphonate and aldol condensation strategies. Reduction of the C-20 ketone and simple protecting group operations then completed the synthesis of bryostatin 2. This flexible approach should provide access to a series of new analogues of this clinically important marine natural product.

引用

页码：7540 / 7552

页数：13

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