Journal of Organic Chemistry p. 1441 - 1450 (1988)
Update date:2022-08-04
Topics:
Paquette, Leo A.
Wiedeman, Paul E.
Bulman-Page, Philip C.
The diterpene antibiotics pleuromutilin and tiamulin have been degraded to the common levorotatory lactone 3 in four steps.This important intermediate has been constructed in optically active condition from simple starting materials.The key elements of this synthesis were (i) stereoselective introduction of the second methyl group in 8 regiospecific cyclopentenone annulation of this oxocyclohexanecarboxylate ester, (ii) stereocontrolled attachment of the lactone ring to give 20, and (iii) proper introduction of the methyl and vinyl substituens α to the lactone carbonyl functionality in 20.This and other synthetic methodologies have been utilized to prepare stereoisomers of 3 that could potentially lead to unnatural pleuromutilins by reconstruction of the cyclooctane ring.
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