Stereocontrolled total synthesis and biological evaluation of (-)- and (+)-petrosin and its derivatives

Hiroki Toya, Takahito Satoh, Kentaro Okano, Kiyosei Takasu, Masataka Ihara, Atsushi Takahashi, Haruo Tanaka, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Total synthesis of (-)- and (+)-petrosin was accomplished. Stereocontrolled construction of the quinolizidine ring was achieved through a diastereoselective Mannich reaction and an aza-Michael reaction. Head-to-tail dimerization was performed by assembly of the two monomers using Suzuki-Miyaura cross coupling and subsequent ring-closing metathesis to construct the 16-membered ring. Biological evaluation of synthetic (-)- and (+)-petrosin and its derivatives indicated that the bispiperidine structure was necessary for the inhibition of syncytium formation.

Original languageEnglish
Pages (from-to)8129-8141
Number of pages13
JournalTetrahedron
Volume70
Issue number43
DOIs
Publication statusPublished - 2014 Oct 28

Keywords

  • Alkaloids
  • HIV
  • Macrocycle
  • Ring-closing metathesis
  • aza-Michael reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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