99529-10-9Relevant academic research and scientific papers
(+)-Pleuromutilin Synthetic Studies. Degradative and de Novo Acquisition of a Levorotatory Tricyclic Lactone Subunit
Paquette, Leo A.,Wiedeman, Paul E.,Bulman-Page, Philip C.
, p. 1441 - 1450 (2007/10/02)
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.
A relay approach to (+)-pleuromutilin. I. De novo synthesis of a levorotatory tricyclic lactone subunit
Paquette,Wiedeman
, p. 1603 - 1606 (2007/10/02)
Construction of an optically active lactone, required for a proposed total synthesis of (+)-pleuromutilin, has been successfully achieved.
