title: Expedient Synthesis of (R)-Patulolide A.
abstract: An efficient derivation of the title compound has been formulated from easily accessible 10-undecenoic acid (1). Thus, dodec-11-en-2-ol (3), prepared from 1, was pyranylated and subjected to bromination with NBS followed by acetolysis to furnish (2E)-1-acetoxy-11-(tetrahydropyranyloxy)dodec-2-ene (5). Its hydrolysis, oxidation, and depyranylation afforded the (2E)-hydroxy ester (9). This, on Candida rugosa lipase-catalyzed acetylation, SeO(2) oxidation, hydrolysis, and Yamaguchi macrolactonization, led to (R)-patulolide A (I) with 67.1% ee. The enantiomeric excess was improved to 97% by first resolving the alcohol 3 via porcine pancreatic lipase catalyzed acetylation and converting the corresponding (R)-acetate (13) to I as done above.
authors.affiliation: Bio-Organic Division, Bhabha Atomic Research Centre, Bombay-400 085, India.
authors.forename: A.
authors.initials: A
authors.lastname: Sharma
authors.forename: S.
authors.initials: S
authors.lastname: Sankaranarayanan
authors.forename: S.
authors.initials: S
authors.lastname: Chattopadhyay