Enantioselective Total Synthesis of (-)-Doliculide Using Catalytic Asymmetric Hydrogenations

被引：5

作者：

Che, Wen ^{[1
,2
]}

Wen, Danyang C. ^{[1
,2
]}

Zhu, Shou-Fei ^{[1
,2
]}

Zhou, Qi-Lin ^{[1
,2
,3
]}

机构：

[1] Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China

[2] Nankai Univ, Coll Chem, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China

[3] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China

来源：

HELVETICA CHIMICA ACTA | 2019年 / 102卷 / 03期

基金：

中国国家自然科学基金;

关键词：

doliculide; natural products; polyketides; total synthesis; asymmetric catalysis; hydrogenation; CYTOTOXIC CYCLODEPSIPEPTIDE; DOLICULIDE; BINDING;

D O I：

10.1002/hlca.201900023

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise and efficient strategy has been developed to construct a polyketide chain by employing relay asymmetric hydrogenations catalyzed by two chiral spiro iridium catalysts. By using this strategy, an enantioselective total synthesis of (-)-doliculide has been achieved in 19 steps with 6.9% overall yield. The route features high enantioselectivity and diastereoselectivity. The catalyst loading can be as low as 0.005mol-%. It is convenient to obtain natural polyketides and their analogues by this strategy.

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页数：10

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