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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 13. Synthesis of CJ-16,264 Analogues (+)-8 and (+)-20a.

Scheme 13

aReagents and conditions: (a) (+)-21 (1.0 equiv), 53 (2.0 equiv), BEt3 (1.3 equiv), toluene, −78 °C, 6 h, 77%; (b) TBAF (1.0 equiv), THF, 0 °C, 5 min, 66%; (c) MnO2 (40 equiv), CH2Cl2, 25 °C, 10 h, 39%, 72% brsm; (d) (+)-21 (1.0 equiv), 90 (2.0 equiv), BEt3 (1.3 equiv), toluene, −78 °C, 6 h, 69%; (e) TBAF (1.0 equiv), THF, 0 °C, 5 min, 67%; (f) MnO2 (40 equiv), CH2Cl2, 25 °C, 10 h, 44%, 66% brsm.