Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 33, Pages 6781-6788Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100888
Keywords
Natural products; Total synthesis; Medicinal chemistry; Polyketides; Aldol reactions; Ring-closing metathesis
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Funding
- Council of Scientific and Industrial Research (CSIR)
- King Saud University, Global Research Network for Organic Synthesis (GRNOS)
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Two aliphatic polyketide natural products, polyrhacitides A and B, have been synthesized in a concise and highly stereo-selective manner. The synthesis involved an auxiliary-based acetate aldol reaction to generate the initial stereogenic center and an iterative Wittig reaction, intramolecular oxa-Michael addition, and chelation-controlled reduction reaction as the key steps to generate additional stereocenters. One-pot acid-mediated global deprotection and cyclization reactions shape the final bicyclic lactone core.
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