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. 2012 Nov 12;4(1):46–51. doi: 10.1021/ml300262e

Scheme 3. Quaternary Substituted Analogues.

Scheme 3

Reagents and conditions: (a) BrCH2CH2OMOM, NaH, THF, 42%. (b) CH=CHCH2Br, KOH, TBAI, MeCN, 77%. (c) DIBAL-H, PhMe. (d) CH=CHCH2NH2, NaBH(OAc)3, 1,2-dichloroethane, 37% for steps c and d. (e) Boc2O, CH2Cl2, 78%. (f) Grubbs II catalyst,10b CH2Cl2, reflux, quan. (g) HCl, MeOH, quan., chiral SFC.