TY - JOUR
T1 - Dihydropyran as a template for lactone synthesis
AU - Brichacek, Matthew P.
AU - Carlson, Robert M
N1 - Copyright:
Copyright 2009 Elsevier B.V., All rights reserved.
PY - 2007/1
Y1 - 2007/1
N2 - 3,4-Dihydro-2H-pyran (DHP) was efficiently transformed into 4-thiophenyl-3,4-dihydro-2H-pyran. This intermediate was converted to the corresponding 1,3-O,S-allylic carbanion with t-butyllithium and selectively alkylated at the carbon α to the sulfur with alkyl halides, an epoxide, and an aldehyde. An one-pot oxidative elimination of the sulfur fragment using vanadium pentoxide generates the desired β-substituted α,β- unsaturated δ-valero lactone.
AB - 3,4-Dihydro-2H-pyran (DHP) was efficiently transformed into 4-thiophenyl-3,4-dihydro-2H-pyran. This intermediate was converted to the corresponding 1,3-O,S-allylic carbanion with t-butyllithium and selectively alkylated at the carbon α to the sulfur with alkyl halides, an epoxide, and an aldehyde. An one-pot oxidative elimination of the sulfur fragment using vanadium pentoxide generates the desired β-substituted α,β- unsaturated δ-valero lactone.
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U2 - 10.1080/00397910701557358
DO - 10.1080/00397910701557358
M3 - Article
AN - SCOPUS:35148816664
SN - 0039-7911
VL - 37
SP - 3541
EP - 3549
JO - Synthetic Communications
JF - Synthetic Communications
IS - 20
ER -