Enantioselective synthesis of the tricyclic core of GKK1032, novel antibiotic anti-tumor agents, by employing an intramolecular Diels-Alder cycloaddition strategy

被引：17

作者：

Asano, M

Inoue, M ^{[1
]}

Katoh, T

机构：

[1] Tokyo Inst Technol, Dept Elect Chem, Yokohama, Kanagawa 2268502, Japan

[2] Sagami Chem Res Ctr, Ayase, Kanagawa 2521193, Japan

[3] Tohoke Pharmaceut Univ, Aoba Ku, Sendai, Miyagi 9818558, Japan

来源：

SYNLETT | 2005年 / 10期

关键词：

Diels-Alder reaction; Stille coupling; natural product synthesis; GKK1032s; antimicrobial agents; anti-tumor agents;

D O I：

10.1055/s-2005-869843

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

An efficient and enantioselective synthesis of a decahydrofluorene nucleus, the tricyclic core (ABC-ring system) of GKK1032s, novel antimicrobial and anti-tumor agents, was achieved using a highly diastereoselective intramolecular Diels-Alder (IMDA) reaction. The substrate for the IMDA reaction was synthesized through intermolecular Diels-Alder reaction of Kitahara-Danishefsky's diene and an enone derived from enulose to construct the functionalized C-ring. CuCl-promoted Stille coupling of a vinyl iodide and a vinylstannane installed the requisite triene side chain.

引用

页码：1539 / 1542

页数：4

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