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. 2014 Jul 14;79(16):7477–7490. doi: 10.1021/jo5012027

Scheme 2. Completion of Syntheses of the 4,6,8,10-Pentamethyldocosanes 2 and 4.

Scheme 2

Reagents and conditions: (i) nBuS(O)2Ph, THF, DMPU, nBuLi, −40 °C, 30 min, 23, −40 °C to rt, 16 h (24, 95%; 31, 90%); (ii) O3, DCM, MeOH, −78 °C, then NaBH4, −78 °C to rt, 16 h (25, 85%; 32, 87%); (iii) Na/Hg, MeOH, rt, 16 h [(S)-26, 73%; (R)-26, 70%]; (iv) TsCl, DMAP, DCM, rt, 16 h [(S)-27, 99%; (R)-27, 98%]; (v) NaI, acetone, reflux, 2 h [(S)-28, 90%; (R)-28, 92%]; (vi) MeS(O)2Ph, THF, nBuLi, −40 °C, 30 min, add 28, rt, 16 h [(S)-29, 73%; (R)-29, 75%]; (vii) nBuLi, hexane, THF, DMPU, −40 °C, 30 min, add 22, −40 °C to rt, 16 h (30, 45%; 33, 34%); (viii) Na/Hg, MeOH, rt, 16 h (2, 83%; 4, 85%).