Diastereoselective Total Synthesis of (±)-Basiliolide B and (±)-epi-8-Basiliolide B

Xuefeng Liang; Liyan Zhou; Long Min; Weijian Ye; Wenli Bao; Wenjing Ma; Qianqian Yang; Fangfang Qiao; Xinhao Zhang; Chi Sing Lee

doi:10.1021/acs.joc.6b02921

Diastereoselective Total Synthesis of (±)-Basiliolide B and (±)-epi-8-Basiliolide B

Xuefeng Liang, Liyan Zhou, Long Min, Weijian Ye, Wenli Bao, Wenjing Ma, Qianqian Yang, Fangfang Qiao, Xinhao Zhang^*, Chi Sing Lee^*

^*Corresponding author for this work

Department of Chemistry

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

14 Citations (Scopus)

Abstract

The C8 and C9 stereogenic centers of the basiliolide/transtaganolide family have been established stereoselectively using a cyclopropane ring-opening strategy, which has been studied by DFT calculations of a variety of lithium-chelating models. The highly functionalized intermediates obtained in this strategy were successfully employed for the diastereoselective total synthesis of (±)-basiliolide B and (±)-epi-8-basiliolide B. The decalin core with a lactone bridge was constructed via a 2-pyrone Diels–Alder (DA) cycloaddition, and the unprecedented seven-membered acyl ketene acetal was established by a biomimetic intramolecular O-acylation cyclization.

Original language	English
Pages (from-to)	3463-3481
Number of pages	19
Journal	Journal of Organic Chemistry
Volume	82
Issue number	7
Early online date	15 Mar 2017
DOIs	https://doi.org/10.1021/acs.joc.6b02921
Publication status	Published - 7 Apr 2017

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@article{81fe278d5bea456b9a84c349849e7409,

title = "Diastereoselective Total Synthesis of (±)-Basiliolide B and (±)-epi-8-Basiliolide B",

abstract = "The C8 and C9 stereogenic centers of the basiliolide/transtaganolide family have been established stereoselectively using a cyclopropane ring-opening strategy, which has been studied by DFT calculations of a variety of lithium-chelating models. The highly functionalized intermediates obtained in this strategy were successfully employed for the diastereoselective total synthesis of (±)-basiliolide B and (±)-epi-8-basiliolide B. The decalin core with a lactone bridge was constructed via a 2-pyrone Diels–Alder (DA) cycloaddition, and the unprecedented seven-membered acyl ketene acetal was established by a biomimetic intramolecular O-acylation cyclization.",

author = "Xuefeng Liang and Liyan Zhou and Long Min and Weijian Ye and Wenli Bao and Wenjing Ma and Qianqian Yang and Fangfang Qiao and Xinhao Zhang and Lee, {Chi Sing}",

note = "This work is supported by the National Natural Science Foundation of China (21232001, 21272012, 21572006), Ministry of Science and Technology of China (2013CB911501), Shenzhen Science, Technology and Innovation Committee (JCYJ20140509093817686, JCYJ20150626111042525), and the Peking University Shenzhen Graduate School. A special acknowledgement is made to Dr. Wesley Ting-kwok Chan (Hong Kong Polytechnic University) and Prof. Hao Xie (Peking University Shenzhen Graduate School) for the X-ray crystallography of compounds 1 and 6 respectively. Publisher Copyright: {\textcopyright} 2017 American Chemical Society",

year = "2017",

month = apr,

day = "7",

doi = "10.1021/acs.joc.6b02921",

language = "English",

volume = "82",

pages = "3463--3481",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "7",

}

TY - JOUR

T1 - Diastereoselective Total Synthesis of (±)-Basiliolide B and (±)-epi-8-Basiliolide B

AU - Liang, Xuefeng

AU - Zhou, Liyan

AU - Min, Long

AU - Ye, Weijian

AU - Bao, Wenli

AU - Ma, Wenjing

AU - Yang, Qianqian

AU - Qiao, Fangfang

AU - Zhang, Xinhao

AU - Lee, Chi Sing

N1 - This work is supported by the National Natural Science Foundation of China (21232001, 21272012, 21572006), Ministry of Science and Technology of China (2013CB911501), Shenzhen Science, Technology and Innovation Committee (JCYJ20140509093817686, JCYJ20150626111042525), and the Peking University Shenzhen Graduate School. A special acknowledgement is made to Dr. Wesley Ting-kwok Chan (Hong Kong Polytechnic University) and Prof. Hao Xie (Peking University Shenzhen Graduate School) for the X-ray crystallography of compounds 1 and 6 respectively. Publisher Copyright: © 2017 American Chemical Society

PY - 2017/4/7

Y1 - 2017/4/7

N2 - The C8 and C9 stereogenic centers of the basiliolide/transtaganolide family have been established stereoselectively using a cyclopropane ring-opening strategy, which has been studied by DFT calculations of a variety of lithium-chelating models. The highly functionalized intermediates obtained in this strategy were successfully employed for the diastereoselective total synthesis of (±)-basiliolide B and (±)-epi-8-basiliolide B. The decalin core with a lactone bridge was constructed via a 2-pyrone Diels–Alder (DA) cycloaddition, and the unprecedented seven-membered acyl ketene acetal was established by a biomimetic intramolecular O-acylation cyclization.

AB - The C8 and C9 stereogenic centers of the basiliolide/transtaganolide family have been established stereoselectively using a cyclopropane ring-opening strategy, which has been studied by DFT calculations of a variety of lithium-chelating models. The highly functionalized intermediates obtained in this strategy were successfully employed for the diastereoselective total synthesis of (±)-basiliolide B and (±)-epi-8-basiliolide B. The decalin core with a lactone bridge was constructed via a 2-pyrone Diels–Alder (DA) cycloaddition, and the unprecedented seven-membered acyl ketene acetal was established by a biomimetic intramolecular O-acylation cyclization.

U2 - 10.1021/acs.joc.6b02921

DO - 10.1021/acs.joc.6b02921

M3 - Journal article

SN - 0022-3263

VL - 82

SP - 3463

EP - 3481

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 7

ER -

Diastereoselective Total Synthesis of (±)-Basiliolide B and (±)-epi-8-Basiliolide B

Abstract

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