Enantioselective total synthesis of macrolide (+)-neopeltolide?
Organic & Biomolecular Chemistry Pub Date: 2013-10-11 DOI: 10.1039/C3OB41541D
Abstract
The asymmetric total synthesis of the anti-proliferative macrolide (+)-neopeltolide has been completed. The stereochemically defined trisubstituted tetrahydropyran ring was constructed via a catalytic hetero-Diels–Alder reaction creating two new chiral centers in a highly diastereoselective manner. The other key features of this synthesis included Brown's asymmetric allylation to install the requisite C-11 and C-13 stereocenters. The synthesis of the oxazole side chain consisted of a hydrozirconation of an alkynyl stannane to establish the Z stereochemistry, followed by a palladium catalyzed cross coupling to introduce the desired Z olefin in the oxazole side chain.
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Journal Name：Organic & Biomolecular Chemistry
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