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一种用于合成 communesin F 和 perophoramidine 的非对映选择性合成策略。

A diastereodivergent synthetic strategy for the syntheses of communesin F and perophoramidine.

机构信息

The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, United States.

出版信息

Org Lett. 2014 Jun 20;16(12):3316-9. doi: 10.1021/ol5013263. Epub 2014 Jun 9.

Abstract

An efficient, unified, and stereodivergent approach toward communesin F and perophoramidine was examined. The C(3) all-carbon quaternary center of an oxindole was smoothly constructed by base-promoted indolone-malonate alkylation chemistry. The complementary relative stereochemistry of the crucial vicinal quaternary centers found in communesin F and perophoramidine was selectively installed by substrate-controlled decarboxylative allylic alkylations.

摘要

我们考察了一种高效、统一且立体发散的方法来合成 Communesin F 和 Perophoramidine。通过碱促进的吲哚酮-丙二酸盐烷基化反应,我们顺利构建了 Oxindole 的 C(3) 全碳季碳原子中心。通过底物控制的脱羧烯丙基烷基化反应,选择性地引入了 Communesin F 和 Perophoramidine 中关键的相邻季碳原子的互补相对立体化学。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b86b/4068777/0ffd194da0e9/ol-2014-013263_0002.jpg

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