The first total synthesis of (1 lR, 12s) diHETE IS reported. The key step is the highly chemioand stereaselective osmylation of a double bond in a trienyne system selectively complexed by an Fe(CO)3 group.
Stereospecific total synthesis of (5.6)-dihete isomers
β Scribed by Claude Kugel; Jean-Paul Lellouche; Jean-Pierre Beaucourt; Gilles Niel; Jean-Pierre Girard; Jean-Claude Rossi
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 273 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The fist highly practical stereocontrolled synthesis of the four diastereoisomeric (5,6)-DiHETEs is described using the acetonides of D-and L-glyceraldehyde as a source of chirality. Their spectral and physico-chemical properties are also described.
Although known for some years as non enzymatic hydrolysis product of ( 5S,6S )-LTb, the diastereoisomeric ( $6 )-dihydroxy -7,9 -trans -11,14 -cis-eicosatetraenoic acids ( 5,6_DiHETBsl)
π SIMILAR VOLUMES
A stereospecific sequence from the allylic alcohol 3 to the new anti-biotic, cycloeudesmol 2, in 9 steps (21.7% overall yield) is described.