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InI3-catalyzed polyene cyclization of allenes and its application in the total synthesis of seven abietane-type diterpenoids.

ABSTRACT: A novel polyene cyclization using the allene group as the initiator has been successfully developed. This methodology provides an efficient strategy for the construction of an abietane-type tricyclic skeleton with a functionalizable C2-C3 double bond and features a wide substrate scope and excellent stereoselectivities. Potential utility of this approach has been well demonstrated by the collective total synthesis of seven abietane-type diterpenoids. Specifically, (±)-2,3-dihydroxyferruginol and (±)-2,3-dihydroxy-15,16-dinor-ent-pimar-8,11,13-triene were synthesized for the first time.

SUBMITTER: Huo CY

PROVIDER: S-EPMC9710309 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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InI<sub>3</sub>-catalyzed polyene cyclization of allenes and its application in the total synthesis of seven abietane-type diterpenoids.

Huo Chen-Yu CY Zheng Tian-Lu TL Dai Wei-Hao WH Zhang Zi-Hao ZH Wang Jin-Da JD Zhu Dao-Yong DY Wang Shao-Hua SH Zhang Xiao-Ming XM Xu Xue-Tao XT

Chemical science 20221102 46

A novel polyene cyclization using the allene group as the initiator has been successfully developed. This methodology provides an efficient strategy for the construction of an abietane-type tricyclic skeleton with a functionalizable C2-C3 double bond and features a wide substrate scope and excellent stereoselectivities. Potential utility of this approach has been well demonstrated by the collective total synthesis of seven abietane-type diterpenoids. Specifically, (±)-2,3-dihydroxyferruginol and ...[more]

PMID: 36544726

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