SYNTHESIS OF 12-KETE AND ITS 8,9-TRANS-ISOMER

Authors
WANG SS ROKACH J POWELL WS DEKLE C FEINMARK SJ
Citation
Ss. Wang et al., SYNTHESIS OF 12-KETE AND ITS 8,9-TRANS-ISOMER, Tetrahedron letters, 35(24), 1994, pp. 4051-4054
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
24
Year of publication
1994
Pages
4051 - 4054
Database
ISI
SICI code
0040-4039(1994)35:24<4051:SO1AI8>2.0.ZU;2-A
Abstract
The first total synthesis of the highly unstable biological mediator 1 2-ketoeicosatetraenoic acid (12-KETE) 3 and its 8,9-trans-isomer 20 is presented. The strategy focuses on the stable precursor dithiane 13 a nd its conversion to 9 and 20. Biochemical experiments show that the t wo isomers are not interconverted in vivo, raising the possibility tha t the trans-isomer 20 may be formed by a primary biochemical mechanism .