Synthesis of rumphellaone A via epoxy nitrile cyclization

Takafumi Hirokawa, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

The first enantioselective total synthesis of rumphellaone A, a cytotoxic 4,5-seco-caryophyllane isolated from the gorgonian coral Rumphella antipathies, has been achieved from a known olefinic alcohol by a 16-step sequence involving Stork's epoxy nitrile cyclization as the key step to concomitantly install a cyclobutane ring and three contiguous stereogenic centers contained in the molecule.

Original languageEnglish
Pages (from-to)4581-4587
Number of pages7
JournalTetrahedron
Volume68
Issue number24
DOIs
Publication statusPublished - 2012 Jun 17

Keywords

  • Cyclobutane
  • Cytotoxic
  • Epoxy nitrile
  • Rumphellaone
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of rumphellaone A via epoxy nitrile cyclization'. Together they form a unique fingerprint.

Cite this