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. 2016 Jan 14;52(4):800-2.
doi: 10.1039/c5cc09060a.

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

Lachlan M Blair  1 , Jonathan Sperry  1
Affiliations

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

Lachlan M Blair et al. Chem Commun (Camb). .

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.

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