ISSN:
0170-2041
Keywords:
Biprorulus bibax
;
Claisen rearrangement
;
Hemiacetals
;
Lactones
;
Lipases
;
Pheromones
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The enantiomers and the racemate of (3R,4S,1′E)-3,4-bis(1′-butenyl)tetrahydro-2-furanol (1) were synthesized by employing Ireland's ester enolate Claisen rearrangement of 5 as the key reaction to provide the corresponding lactone 3 via 4. Optically active 3 was prepared by employing either chemical asymmetric reduction [12 → (S)-8b] or lipase-mediated asymmetric hydrolysis (9→10) and acetylation (meso-2 → ent-10) as the key transformations. The absolute configuration of the naturally occurring 1 was revised as (3R,4S) on the basis of the chemical asymmetric synthesis of (3S,4R)-3 by starting from (S)-8b of known stereochemistry.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1993199301210
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