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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 15.

Scheme 15

Synthesis of the diversifiable pentacycline precursors 47 and 48 by Michael–Claisen cyclization using the phenyl naphthoate ester 46 and enone 1 as substrates, with deprotonation in situ. Further transformation of 48 by a reductive amination reaction provides a route to 7-dimethylamino-alkylaminomethylpentacyclines, as illustrated by the synthesis of the 7-dimethylamino-azetidinylmethylpentacycline 49.