Synthesis of (-)-fortamine and (+)-2-deoxyfortamine from resolved 3S,4S-N-carbomethoxy-3-aminocyclohexen-4-ol

Spencer Knapp, Mark J. Sebastian, Halasya Ramanathan, Parimal Bharadwaj, Joseph A. Potenza

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

A three step sequence (Scheme I) starting with racemic 3,4-epoxycyclohexene (5) and (S)-α-methylbenzylamine gave 3S,4S-N-carbomethoxy-3-aminocydohexen-4-ol (10) with chromatographic removal of the undesired 3R,4R byproduct. The absolute configuration of 10 was established by x-ray crystallographic analysis of its precursor, 6 (as the HCl salt). Resolved 10 was converted to the aminocyditols (-)-fortamine (1) and (+)-2-deoxyfortamine (2) by efficient routes which parallel those previously developed in the racemic series.

Original languageEnglish (US)
Pages (from-to)3405-3410
Number of pages6
JournalTetrahedron
Volume42
Issue number13
DOIs
StatePublished - 1986

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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