Skip to main content
. 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 12. Synthesis of CJ-16,264 Analogue (+)-18 and (+)-19a.

Scheme 12

aReagents and conditions: (a) (+)-21 (1.0 equiv), 87 (3.0 equiv), BEt3 (1.0 equiv), toluene, −78 °C, 6 h, 83%; (b) TBAF (1.1 equiv), AcOH (1.1 equiv), THF, 0 °C, 15 min, 87%; (c) DMP (2.0 equiv), CH2Cl2, 0 → 25 °C, 3 h, (−)-18 (46%), (+)-19 (11%, one C7′ epimer); (d) IBX (5.0 equiv), EtOAc, 70 °C, 7 h, 83%; (e) DMP (6.0 equiv), CH2Cl2, 25°C, 6 h, 58%.