Total Synthesis of Tryprostatin B: Synthesis and Asymmetric Phase-Transfer-Catalyzed Reaction of Prenylated Gramine Salt

被引：20

作者：

Huisman, Matthew ^{[1
]}

Rahaman, Mizzanoor ^{[1
]}

Asad, Sharif ^{[1
]}

Oehm, Sarah ^{[1
]}

Novin, Sherwin ^{[1
]}

Rheingold, Arnold L. ^{[2
]}

Hossain, M. Mahmun ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem & Biochem, 3210 North Cramer St, Milwaukee, WI 53211 USA

[2] Univ Calif San Diego, Dept Chem & Biochem, 9500 Gilman Dr, La Jolla, CA 92093 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 01期

关键词：

CELL CYCLE INHIBITORS; ENANTIOSELECTIVE SYNTHESIS; ASPERGILLUS-FUMIGATUS; DERIVATIVES; RESISTANCE;

D O I：

10.1021/acs.orglett.8b03593

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and efficient total synthesis of microtubule inhibitor tryprostatin B (1) is described. The key step is the preparation of a diprenylated gramine salt 9a. In this step, the prenyl group is incorporated at the 2-position of the indole moiety by direct lithiation of the Boc-protected gramine. We also developed and optimized the asymmetric phase-transfer-catalyzed reaction with salt 9a to provide the C2-prenyl tryptophan intermediate 2 resulting in 93% enantiomeric excess (ee) and 65% yield. The total synthesis of 1 is done in six steps with 35% overall yield.

引用

页码：134 / 137

页数：4

共 23 条

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