Total synthesis of 1-deoxy-7,8a-di-epi-castanospermine and formal synthesis of pumiliotoxin-251D

Prakash R. Sultane, Amar R. Mohite, Ramakrishna G. Bhat

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

A concise and efficient synthesis of (6R,7S,8R,8aS)-6,7,8- trihydroxyindolizidine (1-deoxy-7,8a-di-epi-castanospermine) 2 is described. The synthesis employs cross metathesis in building the key intermediate 9 and is used effectively in constructing indolizidine skeleton for the total synthesis of 1-deoxy-7,8a-di-epi-castanospermine and also for the bicyclic framework of pumiliotoxin 251D 12, 13. The indolizidine skeleton is achieved in one pot sequence of transformations such as deprotection of Cbz group, reduction of double bond, and cyclization. The configurational and conformational structures of compound 10 are unambiguously confirmed by X-ray analysis.

Original languageEnglish
Pages (from-to)5856-5858
Number of pages3
JournalTetrahedron Letters
Volume53
Issue number44
DOIs
StatePublished - 31 Oct 2012
Externally publishedYes

Keywords

  • Castanospermine
  • Cross-metathesis
  • Cyclization
  • Dihydroxylation
  • Pumiliotoxin
  • Wittig reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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