Studies towards the total synthesis of halichlorine: Asymmetric synthesis of the spiroquinolizidine subunit

Dirk Trauner, Samuel J. Danishefsky

Research output: Contribution to journalArticlepeer-review

Abstract

The C1-C15 spiroquinolizidine subunit (cf. 2) of the marine natural product halichlorine (1) was prepared in 12 steps starting from the known 'Meyers-lactam' 5. The synthesis involves a B-alkyl-Suzuki coupling followed by a highly stereoselective intramolecular Michael addition and an intramolecular Mannich ring closure.

Original languageEnglish (US)
Pages (from-to)6513-6516
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number36
DOIs
StatePublished - Sep 3 1999

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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