Formal Syntheses of (±)-Platensimycin and (±)-Platencin via a Dual-Mode Lewis Acid Induced Cascade Cyclization Approach

Lizhi Zhu; Congshan Zhou; Wei Yang; Shuzhong He; Gui Juan Cheng; Xinhao Zhang; Chi Sing Lee

doi:10.1021/jo401105q

Formal Syntheses of (±)-Platensimycin and (±)-Platencin via a Dual-Mode Lewis Acid Induced Cascade Cyclization Approach

Lizhi Zhu
, Congshan Zhou
, Wei Yang
, Shuzhong He
, Gui Juan Cheng
, Xinhao Zhang^*
, Chi Sing Lee^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

45 Citations (Scopus)

Abstract

A mild and efficient dual-mode Lewis acid induced Diels-Alder (DA)/carbocyclization cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids in one pot with the aid of a theoretical study on the π,σ-Lewis acidities of a variety of Lewis acids. With ZnBr₂ as the dual-mode Lewis acid, a series of substituted enones and dienes underwent DA/carbocyclization cascade cyclization reaction smoothly at room temperature and provided the tricyclic cyclized products in one pot with good yields and high diastereoselectivity. The tricyclic cyclized product has been successfully utilized as a common intermediate for formal syntheses of (±)-platensimycin and (±)-platencin.

Original language	English
Pages (from-to)	7912-7929
Number of pages	18
Journal	Journal of Organic Chemistry
Volume	78
Issue number	16
Early online date	17 Jul 2013
DOIs	https://doi.org/10.1021/jo401105q
Publication status	Published - 16 Aug 2013

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title = "Formal Syntheses of (±)-Platensimycin and (±)-Platencin via a Dual-Mode Lewis Acid Induced Cascade Cyclization Approach",

abstract = "A mild and efficient dual-mode Lewis acid induced Diels-Alder (DA)/carbocyclization cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids in one pot with the aid of a theoretical study on the π,σ-Lewis acidities of a variety of Lewis acids. With ZnBr2 as the dual-mode Lewis acid, a series of substituted enones and dienes underwent DA/carbocyclization cascade cyclization reaction smoothly at room temperature and provided the tricyclic cyclized products in one pot with good yields and high diastereoselectivity. The tricyclic cyclized product has been successfully utilized as a common intermediate for formal syntheses of (±)-platensimycin and (±)-platencin.",

author = "Lizhi Zhu and Congshan Zhou and Wei Yang and Shuzhong He and Cheng, \{Gui Juan\} and Xinhao Zhang and Lee, \{Chi Sing\}",

note = "This work is supported by the National Natural Science Foundation of China (Grant Nos. 21272012, 21232001, and 21071052), Shenzhen Science and Technology Innovation Commission of People{\textquoteright}s Government of Shenzhen Municipality (ZDSY20120614144410389 and KQTD201103), and the Peking University Shenzhen Graduate School. Special thanks to Prof. Olaf Wiest (University of Notre Dame), Prof. Ga-Lai Sonoe Law, and her student, Mr. Wai-Sum Lo (The Hong Kong Polytechnic University), for their constructive comments on this manuscript. Publisher Copyright: {\textcopyright} 2013 American Chemical Society",

year = "2013",

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doi = "10.1021/jo401105q",

language = "English",

volume = "78",

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journal = "Journal of Organic Chemistry",

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T1 - Formal Syntheses of (±)-Platensimycin and (±)-Platencin via a Dual-Mode Lewis Acid Induced Cascade Cyclization Approach

AU - Zhu, Lizhi

AU - Zhou, Congshan

AU - Yang, Wei

AU - He, Shuzhong

AU - Cheng, Gui Juan

AU - Zhang, Xinhao

AU - Lee, Chi Sing

N1 - This work is supported by the National Natural Science Foundation of China (Grant Nos. 21272012, 21232001, and 21071052), Shenzhen Science and Technology Innovation Commission of People’s Government of Shenzhen Municipality (ZDSY20120614144410389 and KQTD201103), and the Peking University Shenzhen Graduate School. Special thanks to Prof. Olaf Wiest (University of Notre Dame), Prof. Ga-Lai Sonoe Law, and her student, Mr. Wai-Sum Lo (The Hong Kong Polytechnic University), for their constructive comments on this manuscript. Publisher Copyright: © 2013 American Chemical Society

PY - 2013/8/16

Y1 - 2013/8/16

N2 - A mild and efficient dual-mode Lewis acid induced Diels-Alder (DA)/carbocyclization cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids in one pot with the aid of a theoretical study on the π,σ-Lewis acidities of a variety of Lewis acids. With ZnBr2 as the dual-mode Lewis acid, a series of substituted enones and dienes underwent DA/carbocyclization cascade cyclization reaction smoothly at room temperature and provided the tricyclic cyclized products in one pot with good yields and high diastereoselectivity. The tricyclic cyclized product has been successfully utilized as a common intermediate for formal syntheses of (±)-platensimycin and (±)-platencin.

AB - A mild and efficient dual-mode Lewis acid induced Diels-Alder (DA)/carbocyclization cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids in one pot with the aid of a theoretical study on the π,σ-Lewis acidities of a variety of Lewis acids. With ZnBr2 as the dual-mode Lewis acid, a series of substituted enones and dienes underwent DA/carbocyclization cascade cyclization reaction smoothly at room temperature and provided the tricyclic cyclized products in one pot with good yields and high diastereoselectivity. The tricyclic cyclized product has been successfully utilized as a common intermediate for formal syntheses of (±)-platensimycin and (±)-platencin.

UR - https://www.scopus.com/pages/publications/84882295512

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DO - 10.1021/jo401105q

M3 - Journal article

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AN - SCOPUS:84882295512

SN - 0022-3263

VL - 78

SP - 7912

EP - 7929

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 16

ER -

Formal Syntheses of (±)-Platensimycin and (±)-Platencin via a Dual-Mode Lewis Acid Induced Cascade Cyclization Approach

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