Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2006, Issue 9, Pages 2110-2118Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200500961
Keywords
asymmetric dihydroxylation; butyrolactones; alpha-methylene lactones; naphthalene annulation; natural product synthesis; beta,gamma-unsaturated carboxylic esters
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The naturally occurring gamma-lactones (+)-methylenolactocin (13) and its enantiomer, (+)-protolichesterinic acid (14) and its enantiomer, (+)-rocellaric acid (15), and the methylene bis(gamma-lactone) (-)-avenaciohde (16) were synthesized with 95-98% ees in very few steps. Enantiocontrol was imposed by the asymmetric dihydroxylation of trans-configured beta,gamma-unsaturated carboxylic esters (namely compounds 1i, 1j, and 1n) with AD mix-alpha (R) [for the levorotatory target structures, except for (-)-avenaciolide] or AD mix-beta (R) [for the dextrorotatory target structures plus (-)-avenaciolide]. beta,gamma-Unsaturated carboxylic ester le required increased amounts of the oxidant and auxiliary to produce the hydroxy lactone R,R-3e, a precursor of the naphtho-gamma-lactone (+)-9-hydroxyeleutherol (12; 96 % ee).
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