Synthesis of a butyrolactone precursor of an algae nonaether from an enantiopure glycol obtained by Hoppe's chemistry
Homoallyl carbamate 20, (-)-sparteine, and sBuLi gave a lithium derivative which was formylated with DMF giving the crude aldehydocarbamate 19. With lithium aluminum hydride in refluxing THF, this compound provided diol 22 in 90% overall yield and with 96% ee. This material was carried on to the γ-lactone monoethers 13 (benzyl ether) or 14 (trityl ether). These compounds should be precursors for synthesizing the naturally occurring nonaether 7.
Menges, Markus,Brueckner, Reinhard
p. 1023 - 1030
(2007/10/03)
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