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. 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 2.

Scheme 2

Reagents and conditions (a) TBSCl, Et3N, DMAP, CH2Cl2, 23 °C (98%); (b) DIBAL-H, CH2Cl2, –78 °C (quant); (c) PDC, MS4A, CH2Cl2, 23 °C (99%); (d) monomethylmalonate, piperidine, AcOH, MS3A, toluene, 23 °C (92%); (e) (PhO)2P(O)N3, Et3N, MS4A, toluene, 70 °C; BnOH, 70 °C (89%); (f) H2 (45 psi), Rh[(COD)]-(R,R)-DiPAMP]+BF4, MeOH, 23 °C (100%, 96% ee); (g) H2, 10% Pd/C, EtOAc, 23 °C (quant); (h) AllocCl, pyridine, 23 °C (93%); (i) 0.2 M HCl, AcOH, 110 °C; (j) TBSCl, imidazole, DMF, 23 °C (95%).