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48.1.3.3.5 Method 5: The Barton–McCombie Deoxygenation Reaction Using Tributyltin Hydride or Other Metal Hydrides as the Hydrogen-Atom Source

DOI: 10.1055/sos-SD-048-00072

Wicha, J.Science of Synthesis, (200948190.

The free-radical chain reaction of xanthates (dithiocarbonate O,S-esters) with tributyltin hydride, first reported by Barton and McCombie,[‌125‌] provided a basis for the most versatile and reliable method for deoxygenation of secondary alcohols, which is also applicable to primary and tertiary alcohols in certain cases. Various aspects of the BartonMcCombie reaction have been reviewed.[‌3‌‌5‌,‌7‌,‌126‌,‌127‌] Although the invention of this deoxygenation method was stimulated by the need for an efficient synthetic approach to deoxysugars that could be used to modify aminoglycoside antibiotics,[‌128‌,‌129‌] the first experiments were performed on monofunctional sterols.

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Meeeeee Meeeeeeee Meeeeeeeeeee Meeeeee(e) Meeeeeeee 8-e Meee-Meee Meeeeeeeeeee (°M) Mee
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8,8-eeeeee(eeeeeeeeeeeeeeeeeeeeeee) MMMM [‌888‌]
8,8-eeeeee(8-eeeeeeeeeeeeee eeee) MMMM [‌888‌]
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Meeee 8 Meee Meeeeeee eee eee Meeeeeeeeee ee Meeeeeeeeeee Meeeeeeeeee eee eee MeeeeeMeMeeeee Meeeeeee[‌888‌,‌888‌‌888‌,‌888‌,‌888‌‌888‌]

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MM, MM8, eeee MeMe MMe [‌888‌]
MMMMe eeeeeeee-8-ee [‌888‌]
MeMM(M)Me, eeee MMe [‌888‌,‌888‌,‌888‌]
8-MeeMM(M)Me, eeee 8-MeeM [‌888‌]
8-MM8M8MM(M)Me, eeee 8-MM8M8M [‌888‌]
M8M8MM(M)Me, eeee MM8M8 [‌888‌]
MM8, MMMM, eeee M8M8MM MM8M8 [‌888‌]
8-MeM8M8MM(M)Me, eeee 8-MeM8M8M [‌888‌]
MM8, MMMM, eeee 8,8-Me8M8M8MM 8,8-Me8M8M8M [‌888‌]
8,8,8-Me8M8M8MM(M)Me 8,8,8-Me8M8M8M [‌888‌]
M8Me8MM(M)Me MM8Me8 [‌888‌]
MMMM,e eeee MeMM MMe [‌888‌,‌888‌]
MeM, eeee MeMMM MMMe [‌888‌,‌888‌]
MeMe, MMMM MMMe [‌888‌]
MeM(Me)=MMe8Me, eeee M8M Me [‌888‌,‌888‌]
8-(Me8M)M8M8MM, eeee M8M M [‌888‌]
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References