A concise approach to the tricyclic framework of longipinane- and ent-longipinane-type sesquiterpenoids

Min He; Jiuzhou Yi; Gaoyuan Zhao; Peiqi Chen; Dan Long; Xiaojun Hu; Huilin Li; Xingang Xie; Xiaolei Wang; Xuegong She

doi:10.1039/C8QO01235K

A concise approach to the tricyclic framework of longipinane- and ent-longipinane-type sesquiterpenoids†

Min He,^a Jiuzhou Yi,^a Gaoyuan Zhao,^a Peiqi Chen,^a Dan Long,^a Xiaojun Hu,^a Huilin Li,^a Xingang Xie,

^a Xiaolei Wang^a and Xuegong She

*^a

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* Corresponding authors

^a State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou, China
E-mail: shexg@lzu.edu.cn

Abstract

A concise and efficient strategy for the synthesis of the common 6,6-dimethyltricyclic[5.4.0.0^2,8]undecane framework of longipinane- and ent-longipinane-type sesquiterpenoids has been developed. This approach features an intramolecular Diels–Alder reaction to construct the 6/7 cis-fused ring system and a Ti(III)-mediated reductive radical cyclization reaction to access the highly strained bridged cyclobutane moiety.

Organic Chemistry Frontiers

A concise approach to the tricyclic framework of longipinane- and ent-longipinane-type sesquiterpenoids†

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A concise approach to the tricyclic framework of longipinane- and ent-longipinane-type sesquiterpenoids

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