. 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 2.

Key Protiodesilylation Reactions Directed Toward Natural Product Syntheses

Entry	Substrate	product (all Si→ H)	cond.A	cond.B
1	27	34	<10%	91%
2	28	35	<10%	97%
3	7	9	0–48%	90%
4	29	36	41%	87%
5	30,β–H_A,R=C₁₀H₂₁	37	< 20%	60%
6	31,β–H_A,R=	38	0–40%	55%
7	32,α–H_A,R=	39	0–50%	72%
8	33	40	76%	77%

A: 18-crown-6 (1 equiv.), KOtBu (5%), DMSO/H₂O (19:1), 95 °C, nBu₄NF (6 equiv.), 1–4 d

B: TBAF (6 equiv.), DMF/THF, 75 °C, 4–16 hr