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. Author manuscript; available in PMC: 2011 Nov 21.
Published in final edited form as: Chem Sci. 2010 Jun 11;1(2):202–205. doi: 10.1039/C0SC00284D

Scheme 3.

Scheme 3

Synthesis of the [3.3.1] bicyclic core of 1 via a stereodivergent intramolecular oxidative ketone allylation. Conditions: (a) Mn(OAc)3·2H2O, Cu(OAc)2·H2O, 80–100 °C, AcOH–benzene (1:3), 12a: 57%, 12b: 51% (1.4:1 dr); (b) NaBH4, MeOH; (c) LiAlH4, Et2O, 0 °C, 13a: 87% (2 steps), 13b: 73% (2 steps); (d) Martin sulfurane, benzene, 80 °C, 14a: 23%, 14b: 34%.