A diastereoselective synthesis of both quercus lactone isomers employing allyl-type organometallics as key intermediates

Consecutive treatment of endo-butenylpotassium or endo-1-(tetrahydropyranyloxy)-exo-butenyllithium with FB(OMe)2 and pentanal at -75 Deg affords an erythro- and, threo-adduct, resp., which on hydrolysis and oxidn. lead to cis- and, trans-5-butyl-4-methyl-tetrahydro-2-furanone (4-butyl-3-methyl-4-butanolide), (I), the so-called quercus or oak lactones, resp. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 25, 40, 4491-4
Year:
1984
Keywords:
Note:
CAN 102:24347
26-9
Biomolecules and Their Synthetic Analogs
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0040-4039
written in English.
39638-67-0P; 55013-32-6P Role: SPN (Synthetic preparation), PREP (Preparation) (diastereoselective prepn. of); 70585-62-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and dehydrogenation of); 93828-03-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydroboration-oxidn. of); 93828-05-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrolysis of); 93828-06-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and oxidn. of); 110-62-3 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with butenyldimethoxyboron); 76347-11-0; 93828-04-7 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with pentanal)
Laboratories:




 Record created 2006-03-03, last modified 2018-12-03


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)