Scalable Synthesis of (-)-Rasfonin Enabled by a Convergent Enantioselective α-Hydroxymethylation Strategy

被引：2

作者：

Boeckman, Robert K., Jr. ^{[1
]}

Niziol, Justin M. ^{[1
]}

Biegasiewicz, Kyle F. ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 16期

关键词：

DIMETHYL-SULFOXIDE; RASFONIN; ALCOHOLS; LACTONIZATION; APOPTOSIS; AUTOPHAGY; OXIDATION;

D O I：

10.1021/acs.orglett.8b02222

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A scalable synthesis of the potent antitumor agent, (-)-rasfonin, has been achieved. The synthetic strategy features a highly convergent approach based on a single protocol construction of both major fragments via catalytic enantioselective alpha-hydroxymethylation of simple aliphatic aldehydes. The route described has been successful in the generation of gram quantities of the natural product and serves as the first synthetic strategy to provide sufficient material to continue studies related to its mechanism of action and potential as a cancer therapeutic.

引用

页码：5062 / 5065

页数：4

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