Revision of the structure of haliclorensin to (S)-7-methyl-1,5-diazacyclotetradecane and confirmation of the new structure by synthesis

Markus R. Heinrich, Yoel Kashman, Peter Spiteller, Wolfgang Steglich

Research output: Contribution to journalArticlepeer-review

Abstract

A reinvestigation of the marine alkaloid haliclorensin led to a revision of the proposed structure to 7-methyl-1,5-diazacyclotetradecane. The new structure was confirmed by total synthesis of both optical forms. According to chiroptical measurements and GC-MS investigations, natural haliclorensin consists of a 3:1 mixture of the (S)- and (R)-enantiomers.

Original languageEnglish
Pages (from-to)9973-9978
Number of pages6
JournalTetrahedron
Volume57
Issue number50
DOIs
StatePublished - 10 Dec 2001

Keywords

  • Alkaloids
  • Haliclorensin
  • Marine metabolites
  • Metathesis
  • Stereochemistry

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