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. Author manuscript; available in PMC: 2009 Dec 31.
Published in final edited form as: J Am Chem Soc. 2008 Dec 31;130(52):17913–17927. doi: 10.1021/ja806629e

Scheme 6.

Scheme 6

Synthesis of 6-(S)-carbomethoxysancycline (26) by Michael–Claisen cyclization using the methyl phenyl diester 25 and enone 1 as substrates, with deprotonation in situ, followed by deprotection; in one experiment conducted with the corresponding benzyl phenyl diester 27 as the D-ring precursor, a diastereomeric mixture of cyclization products was obtained.