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Synthesis 2012; 44(19): 3077-3084
DOI: 10.1055/s-0032-1317164
DOI: 10.1055/s-0032-1317164
paper
Studies Directed Towards the Synthesis of Bryostatin: A Stereoselective Synthesis of the C7–C16 Fragment
Further Information
Publication History
Received: 22 June 2012
Accepted after revision: 02 August 2012
Publication Date:
29 August 2012 (online)
Abstract
A stereocontrolled asymmetric synthesis of the C7–C16 fragment of bryostatins is described. The key steps involved were a Jacobsen’s hydrolytic kinetic resolution and a Reformatsky reaction to build the C11–C16 fragment. A vinyl Grignard reagent was used to construct the C7–C10 fragment. The C11–C16 and C7–C10 fragments were coupled by means of a cross-metathesis reaction to give a key intermediate. The pyran ring system was constructed by means of an oxa-Michael reaction.
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