Scheme 5.
Transformation of (R)-alcohol 8 into (R)-lactone 4. Reagents and Conditions: (i) (CH3CO)2O, py, rt, 2 h, 86%; (ii) RuCl3, NaIO4, CH3CN, ClCH2CH2Cl, H2O, 70 °C, 3 h, 84%; (iii) K2CO3, CH3OH, reflux, 3 h; (iv) 1M HCl, rt, overnight, 77% from 13; (v) (COCl)2, (R)-(+)-α-phenylethylamine, CH2Cl2.
