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. Author manuscript; available in PMC: 2018 Nov 8.
Published in final edited form as: J Am Chem Soc. 2017 Oct 24;139(44):15868–15877. doi: 10.1021/jacs.7b08749

Scheme 3. Total Synthesis of CJ-16,264 [(+)-1]a.

Scheme 3

aReagents and conditions: (a) (+)-21 (1.0 equiv), (−)-22 (2.0 equiv), BEt3 (1.1 equiv), toluene, −78 °C, 6 h, 82%; (b) TBAF (1.0 equiv), AcOH (1.05 equiv), THF, 0 °C, 30 min, 88%; (c) IBX (5.0 equiv), EtOAc, 70 °C, 9 h, 68%; (d) DMP (1.5 equiv), CH2Cl2, 0 → 25 °C, 2 h, 83%; BEt3 = triethyl borane, IBX = 2-iodoxybenzoic acid, DMP = Dess–Martin periodinane.