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 language | English |
|---|---|
| Pages (from-to) | 1201-1214 |
| Number of pages | 14 |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 26 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 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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Cite this
Harayama, T., Cho, H., & Inubushi, Y. (1978). Total Synthesis of dl-Chamaecynone a Termiticidal Norsesquiterpene. Chemical and Pharmaceutical Bulletin, 26(4), 1201-1214. https://doi.org/10.1248/cpb.26.1201