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. Author manuscript; available in PMC: 2014 Jun 24.
Published in final edited form as: Tetrahedron. 2013 Apr 15;69(25):5205–5220. doi: 10.1016/j.tet.2013.04.041

Scheme 21.

Scheme 21

Elaboration of the bromo-oxepane moiety for fragment coupling. Reagents and conditions: a) (i) L-(+)-DET, Ti(OiPr)4, tBuOOH, 4 Å MS, CH2Cl2, −23 °C; (ii) Amano lipase-PS, vinyl acetate, Et2O, 0 °C, 99% ee, 41% from nerol; (iii) K2CO3, MeOH, rt, 99%; b) Boc2O, 1-Meimid, 0 °C to rt, 77%; c) Br(coll)2BF4, 4 Å MS, MeNO2, 0 °C, 22%; d) NaOH, MeOH, rt; e) SO3•pyr, DMSO, Et3N, CH2Cl2, 0 °C to rt; 74% (2 steps from ent-79); f) dimethyl-1-diazo-2-oxopropylphosphate, K2CO3, MeOH, rt; g) TMSOTf, 2,6-lutidine, CH2Cl2, 0 °C, 59% (2 steps from 86).