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. Author manuscript; available in PMC: 2011 Dec 15.
Published in final edited form as: Tetrahedron Lett. 2010 Dec 15;51(50):6485–6488. doi: 10.1016/j.tetlet.2010.09.137

Table 1.

Synthesis of desketoraloxifene analogs 3 and 4a

graphic file with name nihms-251655-t0001.jpg

Entry 2 R Product 3/4 Yield (%)d
1 2a R1,R5 = OMe graphic file with name nihms-251655-t0002.jpg 3a 89
2 2a R1,R5 = OH 4a b 58
3 2b R1,R4 = OMe graphic file with name nihms-251655-t0003.jpg 3b 86
4 2b R1,R4 = OH 4b b 61
5 2c R1,R3 = OMe graphic file with name nihms-251655-t0004.jpg 3c 87
6 2c R1,R3 = OH 4c b 52
7 2d R1,R4,R6 = OMe graphic file with name nihms-251655-t0005.jpg 3d 83
8 2d R1,R4,R6 = OH 4d c 39
9 2e R2,R5 = OMe graphic file with name nihms-251655-t0006.jpg 3e 83
10 2e R2,R5 = OH 4e (VI) b 78
11 2f R1,R2,R5 = OMe graphic file with name nihms-251655-t0007.jpg 3f 76
12 2f R1,R2,R5 = OH 4f c 41
a

Reagents and conditions: i. Mitsunobu coupling: 2 (0.2 mmol), alkylaminoethanol (1.5 equiv), DIAD (1.5 equiv), PPh3 (2.0 equiv), THF (2.0 mL), rt, 24–36 h. ii. Demethylation: 3 (0.1 mmol), BBr3, CH2C12 (1.0 mL), rt, N2, 3 h.

b

4.0 Equiv of BBr3 used.

c

6.0 Equiv of BBr3 used.

d

Isolated yields after column chromatography. All isolated products were characterized by 1H and 13C NMR spectroscopy (see the Supporting Information).