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(4bS,8aS)-1-异丙基-4b,8,8-三甲基-4b,5,6,7,8,8a,9,10-八氢菲-2-基乙酸酯

(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa-hydro-phenan-thren-2-yl acetate.

作者信息

Oubabi Radouane, Auhmani Aziz, Ait Itto My Youssef, Auhmani Abdelwahed, Daran Jean-Claude

机构信息

Laboratoire de Synthése Organique et Physico-Chimie Moléculaire, Département de Chimie, Faculté des Sciences, Semlalia, BP 2390, Marrakech 40000, Morocco.

Laboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France.

出版信息

Acta Crystallogr Sect E Struct Rep Online. 2014 Feb 19;70(Pt 3):o317. doi: 10.1107/S1600536814002748. eCollection 2014 Mar 1.

Abstract

The hemisynthesis of the title compound, C22H32O2, was carried out through direct acetyl-ation reaction of the naturally occurring diterpene totarol [systematic name: (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexa-hydro-phen-an-thren-2-ol]. The mol-ecule is built up from three fused six membered rings, one saturated and two unsaturated. The central unsaturated ring has a half-chair conformation, whereas the other unsaturated ring displays a chair conformation. The absolute configuration is deduced from the chemical pathway. The value of the Hooft parameter [-0.10 (6)] allowed this absolute configuration to be confirmed.

摘要

通过天然存在的二萜托塔酚[系统名称:(4bS,8aS)-4b,8,8-三甲基-1-丙-2-基-5,6,7,8a,9,10-六氢菲-2-醇]的直接乙酰化反应,进行了标题化合物C22H32O2的半合成。该分子由三个稠合的六元环构成,一个饱和环和两个不饱和环。中心不饱和环具有半椅式构象,而另一个不饱和环呈椅式构象。绝对构型由化学途径推导得出。胡夫特参数的值[-0.10(6)]使该绝对构型得以确认。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/855a/3998421/8ad362630235/e-70-0o317-fig1.jpg

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