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|Title:||Synthesis of allahabadolactone A||Authors:||Wang, Kongchen
Bates, Roderick Wayland
|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.||URI:||https://hdl.handle.net/10356/88952
|ISSN:||0022-3263||DOI:||http://dx.doi.org/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 https://doi.org/10.1021/acs.joc.7b02368.||Fulltext Permission:||open||Fulltext Availability:||With Fulltext|
|Appears in Collections:||SPMS Journal Articles|
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