Tunable Cyclization Strategy for the Synthesis of Zizaene-, allo-Cedrane-, seco-Kaurane-, and seco-Atesane-Type Skeletons

Qianqian Yang; Wenjing Ma; Gaopeng Wang; Wenli Bao; Xiaoshu Dong; Xuefeng Liang; Lizhi Zhu; Chi Sing Lee

doi:10.1021/acs.orglett.7b02610

Tunable Cyclization Strategy for the Synthesis of Zizaene-, allo-Cedrane-, seco-Kaurane-, and seco-Atesane-Type Skeletons

Qianqian Yang
, Wenjing Ma
, Gaopeng Wang
, Wenli Bao
, Xiaoshu Dong
, Xuefeng Liang
, Lizhi Zhu^*
, Chi Sing Lee^*

^*Corresponding author for this work

Department of Chemistry

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

5 Citations (Scopus)

Abstract

A versatile Lewis acid-mediated cyclization strategy has been developed for selectively establishing zizaene-, allo-cedrane-, seco-kaurane-, and seco-atesane-type skeletons. The zizaene- and seco-atesane-type skeletons can be obtained in a cascade manner, which involves Diels–Alder reaction of cyclic enones with bis-silyloxy dienes and carbocyclization of yne–enolates through Lewis acid dependent 5- or 6-exo-dig modes. This cyclization strategy was also employed for the core synthesis of tashironin.

Original language	English
Pages (from-to)	5324-5327
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.7b02610
Publication status	Published - Oct 2017

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@article{4a60c5f1449c47499df6b8121fe2d1b3,

title = "Tunable Cyclization Strategy for the Synthesis of Zizaene-, allo-Cedrane-, seco-Kaurane-, and seco-Atesane-Type Skeletons",

abstract = "A versatile Lewis acid-mediated cyclization strategy has been developed for selectively establishing zizaene-, allo-cedrane-, seco-kaurane-, and seco-atesane-type skeletons. The zizaene- and seco-atesane-type skeletons can be obtained in a cascade manner, which involves Diels–Alder reaction of cyclic enones with bis-silyloxy dienes and carbocyclization of yne–enolates through Lewis acid dependent 5- or 6-exo-dig modes. This cyclization strategy was also employed for the core synthesis of tashironin. ",

author = "Qianqian Yang and Wenjing Ma and Gaopeng Wang and Wenli Bao and Xiaoshu Dong and Xuefeng Liang and Lizhi Zhu and Lee, \{Chi Sing\}",

note = "We gratefully thank the NSFC (National Natural Science Foundation of China, Nos. 21502002 and 21572006), Chinese Postdoctoral Science Foundation (2015M580910), the SSTIC (Shenzhen Science and Technology Innovation Committee, JSGG20160301103446375, JCYJ20160330095659560, and JCYJ20150626111042525), and Peking University Shenzhen Graduate School for the financial support. Special acknowledgement is made to Dr. Wesley Ting-kwok Chan (Hong Kong Polytechnic University) for the X-ray crystallography of compounds (±)-5b, (±)-11a, (±)-17b, (±)-22, and (±)-24. Publisher Copyright: {\textcopyright} 2017 American Chemical Society",

year = "2017",

month = oct,

doi = "10.1021/acs.orglett.7b02610",

language = "English",

volume = "19",

pages = "5324--5327",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Tunable Cyclization Strategy for the Synthesis of Zizaene-, allo-Cedrane-, seco-Kaurane-, and seco-Atesane-Type Skeletons

AU - Yang, Qianqian

AU - Ma, Wenjing

AU - Wang, Gaopeng

AU - Bao, Wenli

AU - Dong, Xiaoshu

AU - Liang, Xuefeng

AU - Zhu, Lizhi

AU - Lee, Chi Sing

N1 - We gratefully thank the NSFC (National Natural Science Foundation of China, Nos. 21502002 and 21572006), Chinese Postdoctoral Science Foundation (2015M580910), the SSTIC (Shenzhen Science and Technology Innovation Committee, JSGG20160301103446375, JCYJ20160330095659560, and JCYJ20150626111042525), and Peking University Shenzhen Graduate School for the financial support. Special acknowledgement is made to Dr. Wesley Ting-kwok Chan (Hong Kong Polytechnic University) for the X-ray crystallography of compounds (±)-5b, (±)-11a, (±)-17b, (±)-22, and (±)-24. Publisher Copyright: © 2017 American Chemical Society

PY - 2017/10

Y1 - 2017/10

N2 - A versatile Lewis acid-mediated cyclization strategy has been developed for selectively establishing zizaene-, allo-cedrane-, seco-kaurane-, and seco-atesane-type skeletons. The zizaene- and seco-atesane-type skeletons can be obtained in a cascade manner, which involves Diels–Alder reaction of cyclic enones with bis-silyloxy dienes and carbocyclization of yne–enolates through Lewis acid dependent 5- or 6-exo-dig modes. This cyclization strategy was also employed for the core synthesis of tashironin.

AB - A versatile Lewis acid-mediated cyclization strategy has been developed for selectively establishing zizaene-, allo-cedrane-, seco-kaurane-, and seco-atesane-type skeletons. The zizaene- and seco-atesane-type skeletons can be obtained in a cascade manner, which involves Diels–Alder reaction of cyclic enones with bis-silyloxy dienes and carbocyclization of yne–enolates through Lewis acid dependent 5- or 6-exo-dig modes. This cyclization strategy was also employed for the core synthesis of tashironin.

U2 - 10.1021/acs.orglett.7b02610

DO - 10.1021/acs.orglett.7b02610

M3 - Journal article

SN - 1523-7060

VL - 19

SP - 5324

EP - 5327

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Tunable Cyclization Strategy for the Synthesis of Zizaene-, allo-Cedrane-, seco-Kaurane-, and seco-Atesane-Type Skeletons

Abstract

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