30346-27-1Relevant academic research and scientific papers
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)
Mori, Kenji,Itou, Masamichi
, p. 969 - 974 (2007/10/02)
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.
HIGHLY STEROSELECTIVE SYNTHESIS OF EXOCYCLIC ALKENES VIA CYCLIALKYLATION
Negishi, Ei-ichi,Zhang, Yantao,Bagheri, Vahid
, p. 5793 - 5796 (2007/10/02)
Treatment of stereodefined ω-halo-2-iodoalkene derivatives (1), prepared via stereoselective addition reactions of alkynes, with either n-BuLi (1 equiv) or t-BuLi (2 equiv) can produce exocyclic alkenes whose isomeric purity is essentially 100percent.
THE STEREOSPECIFIC FORMATION OF AN EXOCYCLIC ALKENE BY A CONSECUTIVE RADICAL CYCLIZATION-ELEIMINATION
Harris, Francis L.,Weiler, Larry
, p. 2941 - 2944 (2007/10/02)
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.
SYNTHETIC STUDIES ON THE OCHTODANE TYPE TERPENES I. STEREOSELECTIVE CONSTRUCTION OF THE OCHTODANE SKELETON FROM MYRCENE.
Masaki,Hashimoto,Sakuma,Kaji
, p. 3466 - 3475 (2007/10/02)
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.
NEW OCHTODANE SYNTHESES FROM MYRCENE
Masaki, Yukio,Hashimoto, Kinji,Sakuma, Kazuhiko,Kaji, Kenji
, p. 1481 - 1484 (2007/10/02)
The ochtodane skeleton is formed stereoselectively from myrcene via acid-catalyzed cyclization of the benzenesulfenyl chloride adduct and the epoxide in a biogenetic type fashion.Its application to the syntheses of two ochtodane-type monoterpenes, an aldehyde component of the boll weevil pheromone and a diol found in the red alga Ochtodes crockeri, is reported.
