Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2008, Issue 36, Pages 6213-6224Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800680
Keywords
Macrocycles; Asymmetric synthesis; C-C coupling; Dihydroxylation; Epoxidation; Total synthesis; Regioselectivity
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Funding
- Council of Scientific and Industrial Research (CSIR), New Delhi
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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)
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