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. Author manuscript; available in PMC: 2010 Jul 28.
Published in final edited form as: J Med Chem. 2007 Nov 16;50(25):6299–6302. doi: 10.1021/jm7011062

Scheme 4. aSynthesis and absolute configuration of stereoisomers of laurenditerpenol 1a and ent-1g.

Scheme 4

aReagents and conditions: a) Na-Hg (10%), MeOH, rt, 68%; b) i. LDA, PhSeCl, THF, −78 °C, ii. Py, H2O2, CH2Cl2, H2O, 0 °C, 78%; c) CeCl3, NaBH4, MeOH, 0 °C, 72%.