A Bifunctional Lewis Acid Induced Cascade Cyclization to the Tricyclic Core of ent-Kaurenoids and Its Application to the Formal Synthesis of (±)-Platensimycin

Lizhi Zhu; Yejian Han; Guangyan Du; Chi Sing Lee

doi:10.1021/ol3033412

A Bifunctional Lewis Acid Induced Cascade Cyclization to the Tricyclic Core of ent-Kaurenoids and Its Application to the Formal Synthesis of (±)-Platensimycin

Lizhi Zhu
, Yejian Han
, Guangyan Du
, Chi Sing Lee^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Letter › peer-review

20 Citations (Scopus)

Abstract

A mild and efficient bifunctional Lewis acid induced cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids. With ZnBr₂ as the bifunctional Lewis acid, a series of substituted enones and dienes underwent cascade cyclization smoothly at room temperature and provided the tricyclic products in one pot with good yields (75-91%) and high diastereoselectivity. The cyclized product has been successfully employed for the formal synthesis of (±)-platensimycin.

Original language	English
Pages (from-to)	524-527
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	3
Early online date	17 Jan 2013
DOIs	https://doi.org/10.1021/ol3033412
Publication status	Published - 1 Feb 2013

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title = "A Bifunctional Lewis Acid Induced Cascade Cyclization to the Tricyclic Core of ent-Kaurenoids and Its Application to the Formal Synthesis of (±)-Platensimycin",

abstract = "A mild and efficient bifunctional Lewis acid induced cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids. With ZnBr2 as the bifunctional Lewis acid, a series of substituted enones and dienes underwent cascade cyclization smoothly at room temperature and provided the tricyclic products in one pot with good yields (75-91\%) and high diastereoselectivity. The cyclized product has been successfully employed for the formal synthesis of (±)-platensimycin.",

author = "Lizhi Zhu and Yejian Han and Guangyan Du and Lee, \{Chi Sing\}",

note = "This work is supported by the National Natural Science Foundation of China (Grant No. 21272012), Shenzhen Science and Technology Innovation Commission of the People{\textquoteright}s Government of Shenzhen Municipality (ZDSY20120614144410389), and the Peking University Shenzhen Graduate School. Publisher Copyright: {\textcopyright} 2013 American Chemical Society",

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T1 - A Bifunctional Lewis Acid Induced Cascade Cyclization to the Tricyclic Core of ent-Kaurenoids and Its Application to the Formal Synthesis of (±)-Platensimycin

AU - Zhu, Lizhi

AU - Han, Yejian

AU - Du, Guangyan

AU - Lee, Chi Sing

N1 - This work is supported by the National Natural Science Foundation of China (Grant No. 21272012), Shenzhen Science and Technology Innovation Commission of the People’s Government of Shenzhen Municipality (ZDSY20120614144410389), and the Peking University Shenzhen Graduate School. Publisher Copyright: © 2013 American Chemical Society

PY - 2013/2/1

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N2 - A mild and efficient bifunctional Lewis acid induced cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids. With ZnBr2 as the bifunctional Lewis acid, a series of substituted enones and dienes underwent cascade cyclization smoothly at room temperature and provided the tricyclic products in one pot with good yields (75-91%) and high diastereoselectivity. The cyclized product has been successfully employed for the formal synthesis of (±)-platensimycin.

AB - A mild and efficient bifunctional Lewis acid induced cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids. With ZnBr2 as the bifunctional Lewis acid, a series of substituted enones and dienes underwent cascade cyclization smoothly at room temperature and provided the tricyclic products in one pot with good yields (75-91%) and high diastereoselectivity. The cyclized product has been successfully employed for the formal synthesis of (±)-platensimycin.

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DO - 10.1021/ol3033412

M3 - Letter

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SN - 1523-7060

VL - 15

SP - 524

EP - 527

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

A Bifunctional Lewis Acid Induced Cascade Cyclization to the Tricyclic Core of ent-Kaurenoids and Its Application to the Formal Synthesis of (±)-Platensimycin

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