Formal synthesis of tubelactomicins via a transannular Diels-Alder approach

被引：10

作者：

Anzo, Toshimi ^{[1
]}

Suzuki, Akari ^{[1
]}

Sawamura, Kiyoto ^{[1
]}

Motozaki, Toru ^{[1
]}

Hatta, Madoka ^{[1
]}

Takao, Ken-ichi ^{[1
]}

Tadano, Kin-ichi ^{[1
]}

机构：

[1] Keio Univ, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 48期

关键词：

tubelactomicins; macrolide antibiotics; transannular Diels-Alder reaction; hiyama coupling; ring-closing olefin metathesis;

D O I：

10.1016/j.tetlet.2007.10.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A formal synthesis of the antimicrobial tricyclic macrolides, tubelactomicins A and E, featured by a transannular Diels-Alder (TADA) approach, has been explored. The key issue for the transannular cyclization was the synthesis of a 24-membered macrolactone equipped with all the requisite functionalities, which has been achieved using an intramolecular Hiyama cross-coupling strategy. The Hiyama coupling reaction spontaneously triggered off the TADA reaction. From the endo-TADA adduct, formal syntheses of tubelactomicins A and E were achieved. The 24-membered macrolactone formation was also achieved via an intramolecular ring-closing metathesis approach. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：8442 / 8448

页数：7

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