Skip to main content
. Author manuscript; available in PMC: 2012 Dec 23.
Published in final edited form as: Chemistry. 2010 Nov 19;17(3):895–904. doi: 10.1002/chem.201002402

Scheme 5.

Scheme 5

Preparation of C2'-C3' analogues 41 and 48. a Conditions: (a) CH2Cl2/TFA (9:1), 23 °C; 19 (1.7 equiv), HATU (1.3 equiv), iPr2NEt (5.0 equiv), MeCN, 23 °C, 43%. (b) K2CO3 (2.5 equiv), MeOH, 0 °C to 23 °C, 75%. (c) CDI (1.2 equiv), CH2Cl2, 23 °C; morpholine (2–5 equiv), 23 °C, 97% (38) or 94% (43). (d) methacrolein (13–20 equiv), Ru-1 (2 mol%), CH2Cl2 (39) or PhH (46), 23 °C or 50 °C, 74% (39) or 63% (46). (e) Ph3PCH3Br (2.4 equiv), KOtBu (2.3 equiv), THF, 0 °C, 50% (40) or 76% (47). (f) 6 (1.3 equiv), Ru-1 (0.07–0.2 equiv), benzoquinone (0.2–0.5 equiv), DCE, 42–50 °C, 46% (41) or 36% (48). (g) DIBALH (1.1 equiv), CH2Cl2, −78 °C; Ph3P=CHCO2Me (1.5 equiv), 23 °C. (h) H2, Pd/C (2 mol%), EtOAc, 23 °C. (i) NaOH (2.1 equiv), MeOH/H2O (1:1.1), 23 °C, 46% (over 3 steps). (j) 34, CH2Cl2/TFA (9:1), 23 °C; 44 (1.3 equiv), HATU (1.2 equiv), iPr2NEt (3.4 equiv), 23 °C, 66%.