A formal synthesis of l-α-santonin from chiral α,β-epoxyeudesmanolide via enzyme-catalyzed hydrolysis

Article abstract of DOI:10.1248/cpb.42.1160

(4S,5R)-Epoxy-(3S)-hydroxy-(10S)-7α,11βH-eudesman-6α,12-olide 4 and (4R,5S)-epoxy-(3S)-hydroxy-(10R)-7β,11αH-eudesman-6β,12-olide 5 were obtained from (±)-3 using yeast and (3S)-acetoxy-(4S,5R)-epoxy-(10S)- 7α,11βH-eudesman-6α,12-olide 8 was produced from (±)-8 using lipase, respectively. New total synthesis of l-α-santonin (9), and its Δ(4(14))- isomers (10 and 11) were accomplished by a short step synthesis using the optically active key intermediate (10S)-8 (prepared by asymmetric hydrolysis of (±)-8).

Full text of DOI:10.1248/cpb.42.1160

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