A Highly Convergent Cascade Cyclization to cis-Hydrindanes with All-Carbon Quaternary Centers and Its Application in the Synthesis of the Aglycon of Dendronobiloside A

Yejian Han; Lizhi Zhu; Yuan Gao; Chi Sing Lee

doi:10.1021/ol102781p

A Highly Convergent Cascade Cyclization to cis-Hydrindanes with All-Carbon Quaternary Centers and Its Application in the Synthesis of the Aglycon of Dendronobiloside A

Yejian Han
, Lizhi Zhu
, Yuan Gao
, Chi Sing Lee^*

^*Corresponding author for this work

Department of Chemistry

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

29 Citations (Scopus)

Abstract

An efficient and versatile ZnBr₂-catalyzed Diels-Alder/ carbocyclization cascade reaction has been developed for construction of highly functionalized cis-hydrindanes (70-96% yields with high diastereoselectivity), and it has been successfully utilized in the synthesis of the aglycon of dendronobiloside A.

Original language	English
Pages (from-to)	588-591
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	4
Early online date	10 Jan 2011
DOIs	https://doi.org/10.1021/ol102781p
Publication status	Published - 18 Feb 2011

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10.1021/ol102781p

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title = "A Highly Convergent Cascade Cyclization to cis-Hydrindanes with All-Carbon Quaternary Centers and Its Application in the Synthesis of the Aglycon of Dendronobiloside A",

abstract = "An efficient and versatile ZnBr2-catalyzed Diels-Alder/ carbocyclization cascade reaction has been developed for construction of highly functionalized cis-hydrindanes (70-96\% yields with high diastereoselectivity), and it has been successfully utilized in the synthesis of the aglycon of dendronobiloside A.",

author = "Yejian Han and Lizhi Zhu and Yuan Gao and Lee, \{Chi Sing\}",

note = "The financial support for this project from the National Natural Science Foundation of China (Grant No. 20672003) and the Peking University Shenzhen Graduate School is gratefully acknowledged. A special acknowledgment is made to the Hong Kong Polytechnic University, which is funded by the University Grants Committee of Hong Kong Special Equipment Grant, for the 500 and 600 MHz NMR spectrometers. Publisher Copyright: {\textcopyright} 2011 American Chemical Society",

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doi = "10.1021/ol102781p",

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T1 - A Highly Convergent Cascade Cyclization to cis-Hydrindanes with All-Carbon Quaternary Centers and Its Application in the Synthesis of the Aglycon of Dendronobiloside A

AU - Han, Yejian

AU - Zhu, Lizhi

AU - Gao, Yuan

AU - Lee, Chi Sing

N1 - The financial support for this project from the National Natural Science Foundation of China (Grant No. 20672003) and the Peking University Shenzhen Graduate School is gratefully acknowledged. A special acknowledgment is made to the Hong Kong Polytechnic University, which is funded by the University Grants Committee of Hong Kong Special Equipment Grant, for the 500 and 600 MHz NMR spectrometers. Publisher Copyright: © 2011 American Chemical Society

PY - 2011/2/18

Y1 - 2011/2/18

N2 - An efficient and versatile ZnBr2-catalyzed Diels-Alder/ carbocyclization cascade reaction has been developed for construction of highly functionalized cis-hydrindanes (70-96% yields with high diastereoselectivity), and it has been successfully utilized in the synthesis of the aglycon of dendronobiloside A.

AB - An efficient and versatile ZnBr2-catalyzed Diels-Alder/ carbocyclization cascade reaction has been developed for construction of highly functionalized cis-hydrindanes (70-96% yields with high diastereoselectivity), and it has been successfully utilized in the synthesis of the aglycon of dendronobiloside A.

UR - https://www.scopus.com/pages/publications/79951619885

U2 - 10.1021/ol102781p

DO - 10.1021/ol102781p

M3 - Journal article

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AN - SCOPUS:79951619885

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SP - 588

EP - 591

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

A Highly Convergent Cascade Cyclization to cis-Hydrindanes with All-Carbon Quaternary Centers and Its Application in the Synthesis of the Aglycon of Dendronobiloside A

Abstract

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