New synthetic methods for. gamma.-geraniol, boll weevil pheromone, and. alpha.-damascone employing 2-(hydroxymethyl)-4-(phenylthio)-1-butene as a building …

T Mandai, K Mizobuchi, M Kawada…

Index: Mandai, Tadakatsu; Mizobuchi, Koji; Kawada, Mikio; Otera, Junzo Journal of Organic Chemistry, 1984 , vol. 49, # 18 p. 3403 - 3406

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Citation Number: 22

Abstract

11 2 a (i)(CH,), C= CHCH, MgCl, CUI, a, a'-dipyridyl, THF;(ii) H, O,, dioxane;(iii) Ac, O catalyst (CF, CO), O;(iv) NaBH,-EtOH;(v) HC0, H;(vi) PDC, CH, Cl,;(vii) MeONa-MeOH. led us to novel syntheses of several terpenoids such as myrcene, citral, squalane, isophytol, P- ionone, irones, 8-farnesene, 8-sinensal, and dendrolasin. 2 Further, conjugated polyenes and methyl retinoate also have been successfully synthesized by employing 4a. 3 In this ...