Total syntheses of (±)-spiroindimicins B and C enabled by a late-stage Schöllkopf-Magnus-Barton-Zard (SMBZ) reactionElectronic supplementary information (ESI) available: Experimental procedures and compound characterization data. CCDC 1415422. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5cc09060a

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 w...

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Main Authors: Blair, Lachlan M, Sperry, Jonathan
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Summary: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. The total syntheses of the structurally unprecedented alkaloids (±)-spiroindimicins B and C has been achieved.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc09060a