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http://hdl.handle.net/10397/95369
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. |
Appears in Collections: | Journal/Magazine Article |
Files in This Item:
File | Description | Size | Format | |
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Diastereoselective_Total_Synthesis.pdf | Pre-Published version | 2.95 MB | Adobe PDF | View/Open |
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