Highly stereoselective construction of 4,6-cis-substituted quinolizidine ring core: An application to enantioselective total synthesis of the marine alkaloid clavepictines A, B and pictamine

Naoki Toyooka*, Yasuhito Yotsui, Yasuko Yoshida, Takefumi Momose, Hideo Nemoto

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

The enantioselective total synthesis of the marine alkaloids clavepictines A, B and pictamine has been achieved through the highly stereocontrolled quinolizidine ring closure of the conformationally constrained piperidine ring system (2), which bears the chiral centers and appropriate functionality needed for the synthesis of target alkaloids. The absolute stereochemistry of clavepictines and pictamine was verified to be 3R, 4S, 6S, 9aS by the present synthesis.

Original languageEnglish
Pages (from-to)15209-15224
Number of pages16
JournalTetrahedron
Volume55
Issue number52
DOIs
StatePublished - 1999/12/24

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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