%0 Journal Article %J European Journal of Organic Chemistry %D 2008 %T First asymmetric total synthesis of penarolide sulfate A(1) %A Mohapatra, Debendra K. %A Bhattasali, Debabrata %A Gujar, Mukund K. %A Khan, Mohammad Islam %A Shashidhara, K. S. %K Asymmetric synthesis %K C-C coupling %K Dihydroxylation %K epoxidation %K Macrocycles %K Regioselectivity %K Total synthesis %X

Penarolide sulfate A(1), with three contiguous stereogenic centers on a macrocyclic skeleton, affords promise as an alpha-glucosidase inhibitor. Herein, we describe the first asymmetric total synthesis of this natural product. A stereoselective strategy for rapid assembly of the complete framework of the 30-membered macrocyclic core is delineated herein. Sequential amidation and intramolecular Sonogashira cross-coupling reactions were pivotal to the success of our efforts. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

%B European Journal of Organic Chemistry %I WILEY-BLACKWELL %C COMMERCE PLACE, 350 MAIN ST, MALDEN 02148, MA USA %P 6213-6224 %8 DEC %G eng %N 36 %9 Article %3 Foreign %4 3.068 %R 10.1002/ejoc.200800680