Journal of the American Chemical Society p. 2414 - 2428 (1980)
Update date:2022-08-03
Topics:
Schultz, Arthur G.
Godfrey, Jollie D.
An annelation approach to the synthesis of eudesmane sesquiterpenes is described.The 1,6-annelation reagent α-carbomethoxy-β-methyl-γ-methylidene-Δα,β-butenolide (1) is used to construct the linear tricyclic lactone 2,5,6,7,8,8a,9,9aβ-octahydro-8aβ-methyl-2-oxonaphtho<2,3-b>furan-3-carboxylic acid methyl ester (2).The conversion of 2 to dl-dihydrocallitrisin (3), dl-7,8-epialantolactone (4), dl-7,8-epiisoalantolactone (5), and dl-atractylon (6) is detailed.Studies directed toward synthesis of the elemane sesquiterpene lactones vernomenin and vernolepin also are presented.
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