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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 11.

Scheme 11

Synthesis of 10-deoxysancycline (41) by Michael–Claisen cyclization using phenyl 2-(bromomethyl)benzoate 39 and enone 1 as substrates, with deprotonation in situ, followed by deprotection.