Skip to main content
. Author manuscript; available in PMC: 2016 Mar 24.
Published in final edited form as: Nat Prod Rep. 2015 Feb;32(2):328–347. doi: 10.1039/c4np00051j

Scheme 7.

Scheme 7

Reagents and conditions (a) TsCl, TEA, CH2Cl2, 0 °C (83%); (b) Br2, AcOH, CH2Cl2, rt (97%); (c) MeI, K2CO3, acetone, reflux (96%); (d) NaOH, EtOH/H2O, reflux (97%); (e) MOMCl, DIPEA, CH2Cl2, 0 °C (97%); (f) n-BuLi, THF, –60 °C; DMF (79%); (g) HC(OMe)3, CSA, MeOH, rt (94%); (h) n-BuLi, Et2O, 0 °C to rt; I2; (i) conc. HCl, THF, rt (72%, 2 steps); (j) BnBr, K2CO3, CH3CN, reflux (98%); (k) 70, TMG, CH2Cl2, rt (93%); (l) Rh[(COD)-(S,S)-Et-DuPHOS]+OTf−, H2 (500 psi), EtOAc, 50 °C (99%, 94% ee); (m) LiOH, MeOH/H2O/THF, 0 °C to rt (quant).