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Title: Synthesis of allahabadolactone A
Authors: Wang, Kongchen
Bates, Roderick Wayland
Keywords: DRNTU::Science::Chemistry
Hydrogen Peroxide
Issue Date: 2017
Source: Wang, K., & Bates, R. W. (2017). Synthesis of Allahabadolactone A. The Journal of Organic Chemistry, 82(23), 12624-12630. doi:10.1021/acs.joc.7b02368
Series/Report no.: The Journal of Organic Chemistry
Abstract: A synthesis of allahabadolactone A is described employing diastereoselective Diels–Alder and selenocyclization reactions, starting from (R)-citronellal and propylene oxide. The Diels–Alder substrate is built up in an efficient manner by rhodium-catalyzed alkyne hydroboration and palladium-catalyzed coupling reactions of E-1,2-dichloroethene. It is observed that the Diels–Alder reaction only displays high diastereoselectivity when the diene bears an additional alkene substituent but not an alkyne substituent.
ISSN: 0022-3263
DOI: 10.1021/acs.joc.7b02368
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
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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