| Autor: |
Masaki, Yukio, Hashimoto, Kinji, Sakuma, Kazuhiko, Kaji, Kenji |
| Zdroj: |
Bulletin of the Chemical Society of Japan; December 1984, Vol. 57 Issue: 12 p3466-3475, 10p |
| Abstrakt: |
The ochtodane skeleton, the Carbon framework of 1,1-dimethyl-3-ethylcyclohexane (1) was constructed highly stereoselectively by the acid-catalyzed (SnCl4or CF3CO2H) cyclization of the terminally functionalized myrcene derivatives, the benzenesulfenyl chloride adduct (7), the terminal β-hydroxy sulfide (8) derived from 7, and myrcene 6,7-epoxide (10). The stereoselectivity of the 3-exo-double bond in 1formed concomitantly in the cyclization reaction was found to depend remarkably upon the reaction temperature and the 85–94% of E-stereoselectivity was attained at −78 °C. By the method, the ochtodane derivatives with the sulfur- or oxygen-functional groups on the C(6)-position were obtained. Synthetic applications of the ochtodane type compounds (12) and (19) to the aldehyde component (4) of the pheromone of the male boll weevils and to an ochtodane type terpene (26) isolated from the red alga Octodes crockeri, are reported. |
| Databáze: |
Supplemental Index |
| Externí odkaz: |
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