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. Author manuscript; available in PMC: 2012 Feb 9.
Published in final edited form as: Bioorg Med Chem Lett. 2009 Oct 22;19(24):6898–6901. doi: 10.1016/j.bmcl.2009.10.079

Scheme 1.

Scheme 1

Sclerolog Synthesis via an Aldol-Cycloaldol Sequence.

a. 1. LDA, THF, −78 °C. 2. 2a–f. 3. HOAc. b. Ag2O, BrCH2CO2R, DMF, 2,6-lutidine, rt. c. 1. KHMDS, THF, −78 °C. 2. HOAc.

a 2a–d: 2-bromo-, 3-bromo-, 2,3-dichloro-, 2,4-dichlorobenzaldehyde, respectively; 2e: 1-naphthaldehyde; 2f : pyridine-2-carboxaldehyde.