Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/95369
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Title: Diastereoselective total synthesis of (±)-Basiliolide B and (±)-epi-8-Basiliolide B
Authors: Liang, X
Zhou, L
Min, L
Ye, W
Bao, W
Ma, W
Yang, Q
Qiao, F
Zhang, X
Lee, CS
Issue Date: 7-Apr-2017
Source: Journal of organic chemistry, 7 Apr. 2017, v. 82, no. 7, p. 3463-3481
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.
Publisher: American Chemical Society
Journal: Journal of organic chemistry 
ISSN: 0022-3263
EISSN: 1520-6904
DOI: 10.1021/acs.joc.6b02921
Rights: © 2017 American Chemical Society
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.6b02921.
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