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

被引：32
|
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.
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收藏
页码：800 / 802
页数：3
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