Total Synthesis of dl-Chamaecynone a Termiticidal Norsesquiterpene

Takashi Harayama, Hidetsura Cho, Yasuo Inubushi

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

The total synthesis of dl-chamaecynone (1), which has termiticidal activity, has been accomplished. The key compound (30a), which has the same four chiral centers as chamaecynone (1), was obtained in a single step by taking advantage of the Diels-Alder reaction of 5-ethynyl-2-methylcyclohex-2-en-1-one (3) with 1-methoxy-3-trimethylsiloxy-1,3- pentadiene (4). The stereostructure of the major adduct of the Diels-Alder reaction was determined to be the formula (30a) by INDOR experiment. The compound (30a) was converted in four steps into dl-chamaecynone. The preliminary examinations of the Diels-Alder reaction of trans-1-methoxy-3-trimethylsiloxy-1,3-butadiene (2) with 1-carvone and the compound (3) were also carried out, respectively.

Original languageEnglish
Pages (from-to)1201-1214
Number of pages14
JournalChemical and Pharmaceutical Bulletin
Volume26
Issue number4
DOIs
Publication statusPublished - 1978 Jan 1

Keywords

  • 1-methoxy-3-trimethylsiloxy-1,3-pentadiene
  • 5-ethynyl-2-methvlcyclohex-2-en-1-one
  • Diels-Alder reaction
  • INDOR experiment
  • conformational analysis
  • dl-chamaecynone
  • stereochemistry
  • termiticidal activity

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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