Tetrafluorosilane is a mild and very selective reagent for the cleavage of silyl-protected alcohols

Total Synthesis of Gambierol: Subunit Coupling and Completion

“…27 Oxidation of the primary alcohol was followed by the conversion of the resulting aldehyde into the corresponding diiodoalkene using a modified Corey–Fuchs addition reaction (Scheme ) 28. Stereoselective reduction using Zn(Cu) couple,29 global deprotection using SiF 4 ,30 and Stille coupling of the resulting triol with dienyl stannane 53 27 provided (−)‐gambierol. The spectroscopic and physical data for synthetic gambierol was identical to that reported previously.…”

Reactions at Oxygen Atoms

“…Some of the other reagents reported are: BF 3 'Et 2 0 in CHCl 3 (or CH 2 CI 2 ) (0-25 .C) [163] [168] [noteworthy is the fact that phenol TBDMS ethers are unaffected by the reagent (SiF4/CH2Cl2' 24 h, rt)], and triethylamine trihydrofluoride (Et 3 N'3HF) in THF [169]; the last reagent (24 h, rt) is mild enough to retain the base-protecting group (Scheme 6 0). …”

N2O4/SiO2 system as an efficient reagent for rapid and chemoselective conversion of trimethylsilyl ethers to the parent alcohols under nonaqueous conditions

“…There are various methods for regeneration of the parent hydroxy group from the silyl ethers by the use of aqueous HF [6], KF-crown ether [7], BF 3 .Et 2 O [8], N-bromo succinimide [9], CF 3 SO 3 SiMe 3 [10], NH 4 F [11], SiF 4 [12], aqueous acids [13], (n-Bu) 4 NF (TBAF) [14], K 2 CO 3 *Corresponding author. E-mail: zolfi@basu.ac.ir [15], polymer supported -acid [16], Lewis acids [17], K 5 CoW 12 O 40 .3H 2 O [18], and neutral alumina [19].…”