Total syntheses of (±)-spiroindimicins B and C enabled by a late-stage Schollkopf-Magnus-Barton-Zard (SMBZ) reaction

被引：33

作者：

Blair, Lachlan M. ^{[1
]}

Sperry, Jonathan ^{[1
]}

机构：

[1] Univ Auckland, Sch Chem Sci, Auckland 1010, New Zealand

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 04期

关键词：

ALPHA-METALATED ISOCYANIDES; REDUCTIVE HECK CYCLIZATION; SP SCSIO 03032; ORGANIC-SYNTHESIS; OXAZOLYLINDOLE ALKALOIDS; BISINDOLE ALKALOIDS; NATURAL-PRODUCTS; ALLYL-BROMIDES; DEEP; OXIDATION;

D O I：

10.1039/c5cc09060a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The spiroindimicins are a family of structurally unprecedented alkaloids isolated from the deep-sea-derived marine actinomycete Streptomyces sp. SCSIO 03032. The total syntheses of (+/-)-spiroindimicins B and C are disclosed, the first of any member of this family. Central to the successful strategy was installing the spirocentre using a mild intramolecular Heck reaction, the assembly of a pentacyclic spirobisindole by Fischer indolization and a late-stage Schollkopf-Magnus-Barton-Zard (SMBZ) reaction to construct the trisubstituted pyrrole.

引用

页码：800 / 802

页数：3

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