. Author manuscript; available in PMC: 2008 Aug 13.

Published in final edited form as: Org Lett. 2005 Jun 9;7(12):2405–2408. doi: 10.1021/ol0506821

Table 1.

Probing the Role of Neighboring Hydroxyl Assistance in the Protiodesilylation of 19–21

entry	substrate R = SiMe₂Ph	Product R = H	Cond. A	cond. B
1	19	22	85%	83%
2	20	23	92%	82%
3	21	24	91%	83%
4	11	16	47%	86%
5	14α	18α	92%	99%

A: 18-crown-6 (1 equiv.), KOtBu (5%), DMSO/H₂O (19:1), 95 °C, TBAF (6 equiv.), 1–7 d

B: TBAF (3 equiv.), DMF/THF, 75 °C, 4–16 hr