- THE STEREOSPECIFIC FORMATION OF AN EXOCYCLIC ALKENE BY A CONSECUTIVE RADICAL CYCLIZATION-ELEIMINATION
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The iodovinylstannanes 4 and 5 were prepared by the conjugate addition of the tri-n-butyltin moiety to a substituted propiolic ester.Compounds 4 and 5 underwent a radical cyclization-elimination reaction to stereospecifically generate an exocyclic alkene.
- Harris, Francis L.,Weiler, Larry
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- Pheromone Synthesis, CXV. - Synthesis of (Z)-2-Ochtoden-1-ol, (E)-2-Ochtoden-1-al, and (Z)-2-Ochtoden-1-al, the Pheromone Components of the Boll Weevil (Anthonomus grandis)
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The synthesis of geometrically pure (Z)-2-ochtoden-1-ol (1), (E)-2-ochtoden-1-al (2), and (Z)-2-ochtoden-1-al (3) was achieved starting from myrcene.
- Mori, Kenji,Itou, Masamichi
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p. 969 - 974
(2007/10/02)
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- SYNTHETIC STUDIES ON THE OCHTODANE TYPE TERPENES I. STEREOSELECTIVE CONSTRUCTION OF THE OCHTODANE SKELETON FROM MYRCENE.
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The ochtodane skeleton, the Carbon framework of 1,1-dimethyl-3-ethylcyclohexane (1) was constructed highly stereoselectively by the acid-catalyzed (SnCl//4 or CF//3CO//2H) cyclization of the terminally functionalized myrcene derivatives, the benzenesulfenyl chloride adduct (7), the terminal beta -hydroxy sulfide (8) derived from 7, and myrcene 6,7-epoxide (10). The stereoselectivity of the 3-exo-double bond in 1 formed concomitantly in the cyclization reaction was found to depend remarkably upon the reaction temperture and the 85-94% of E-stereoselectivity was attained at minus 78 degree C. By the method, the ochtodane derivatives with the sulfur- or oxygen-functional groups on the C(6)-position were obtained.
- Masaki,Hashimoto,Sakuma,Kaji
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p. 3466 - 3475
(2007/10/02)
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