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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 3.

Scheme 3

Synthesis of minocycline (9) by Michael–Claisen cyclization using the tert-butoxycarbonyl-protected phenyl ester 17 as the D-ring precursor and a stepwise protocol for addition of the base and enone 1, followed by deprotection.