Total Synthesis of (±)-Hyphodermins A and D

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Title Total Synthesis of (±)-Hyphodermins A and D
Author Loughlin, Wendy Anne; Jenkins, Ian Douglas; Henderson, Luke; Campitelli, Marc Ronald; Healy, Peter Conrad
Journal Name Journal of Organic Chemistry
Year Published 2008
Place of publication United States
Publisher American Chemical Society
Abstract An efficient formal synthesis of (()-hyphodermins A and D, metabolites of Hyphoderma radula, has been completed in 12 and 11 steps, respectively. The tricyclic carbon skeleton of enone 6 was rapidly assembled from diester 11 via an R brominationn-elimination sequence followed by anhydride formation. Regioselective reduction of the lactone group of enone 6 with LiAlH(t-BuO)3 gave lactol 15. Lactol 15 was converted in two steps to (()-hyphodermin D, without the need for complex protection-deprotection strategies. Lactol 15 was converted in three steps to (()-hyphodermin A, via the key step of epoxidation of an enone in the presence of a THP lactol. A combination of NMR and ab initio studies suggests that the structures of hyphodermin C and D should be interchanged.
Peer Reviewed Yes
Published Yes
Publisher URI http://pubs.acs.org/journal/joceah
Alternative URI http://dx.doi.org/10.1021/jo800227p
Copyright Statement Copyright 2008 American Chemical Society. Self-archiving of the author-manuscript version is not yet supported by this publisher. The contents of this journal can be freely accessed online via the ACS web page after publication. Use hypertext link above to access the ACS website.
Volume 73
Issue Number 9
Page from 3435
Page to 3440
ISSN 0022-3263
Date Accessioned 2008-10-16
Date Available 2009-02-10T01:42:18Z
Language en_AU
Faculty Faculty of Science, Environment, Engineering and Technology
Subject PRE2009-Organic Chemical Synthesis
URI http://hdl.handle.net/10072/21244
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1

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