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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 7. Synthesis of CJ-16,264 Analogue (±)-11a.

Scheme 7

aReagents and conditions: (a) 62 (3.0 equiv), Grubbs II catalyst 56 (0.2 equiv), CH2Cl2, 25 °C, 24 h, 63%; (b) TBAF (1.0 equiv), AcOH (2.0 equiv), THF, 0 °C, 5 min, 82%; (c) MNBA (1.4 equiv), DMAP (3.0 equiv), CH2Cl2, 25 °C, 12 h, 84%; (d) IBX (5.0 equiv), EtOAc, 70°C, 7 h, 48%; MNBA = 2-methyl-6-nitrobenzoic anhydride, DMAP = N,N-dimethylpyridin-4-amine.