Reagents and conditions: (a) 18 + (COCl)2 (1.1 mol equiv), dimethyl formamide
(cat.), CH2Cl2, rt, 15 h, concentrate and add
to 17, Hunig’s base (2 mol equiv), CH2Cl2, rt, 20 h (75%). (b) (i) dimethyl sulfoxide (2.2 mol
equiv), CH2Cl2, −78 °C, add (COCl)2 (1.1 mol equiv), stir 15 min; (ii) add 19, stir
15 min; (iii) add triethylamine (5 mol equiv) and warm to rt 90 min;
(iv) 20 in CH2Cl2, sodium triacetoxyborohydride
(2 mol equiv), rt (27%).