Total synthesis of (±)-hyphodermins A and D
Data(s) |
02/05/2008
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Resumo |
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 α 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.<br /> |
Identificador | |
Idioma(s) |
eng |
Publicador |
American Chemical Society |
Relação |
http://dro.deakin.edu.au/eserv/DU:30028581/henderson-totalsynthesis-2008.pdf http://dx.doi.org/10.1021/jo800227p |
Direitos |
2008, American Chemical Society |
Tipo |
Journal Article |