C. Fehr, J. Galindo, S. Chappuis
Apr 28, 1992
Citations
0
Influential Citations
7
Citations
Journal
Tetrahedron Letters
Abstract
Abstract The lithium dianion of sorbic acid reacts with hexanal at the C(2)-position to afford separable anti - and syn-hydroxy carboxylic acids 3 and 4 (87%; 3 4 =59:41 or 79%; 3 4 =16:84), whose stereospecific anti-decarboxylative elimination respectively affords (3E, 5Z)- and (3E, 5E)-1,3,5-undecatriene (1) and (2) (cis- and trans-galbanolenes (1 and (2) (69%). An alternative route to 1 involves conversion of 3, 4 to cis-lactone 7 (45% after chromatography) followed by thermal syn-decarboxylation (81%). The described procedure is both new and of general applicability, as illustrated by the synthesis of trienes with different substitution pattern.