Issue 4, 2016

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

Abstract

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 Schöllkopf–Magnus–Barton–Zard (SMBZ) reaction to construct the trisubstituted pyrrole.

Graphical abstract: Total syntheses of (±)-spiroindimicins B and C enabled by a late-stage Schöllkopf–Magnus–Barton–Zard (SMBZ) reaction

Supplementary files

Article information

Article type
Communication
Submitted
02 Nov 2015
Accepted
11 Nov 2015
First published
16 Nov 2015

Chem. Commun., 2016,52, 800-802

Author version available

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

L. M. Blair and J. Sperry, Chem. Commun., 2016, 52, 800 DOI: 10.1039/C5CC09060A

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