ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Reduction of the carbonyl group in the side chain of 4-(1-nitro-2-oxocyclododecyl)butan-2-one (3) with organoboron complexes are influenced by the chiral center, in 4-position with respect to the carbonyl C-atom, to which the NO2 group is attached, a rare type for an asymmetric reduction. Independent of the (R)- or (S)-configuration of the Alpine-Hydride, (+)-3 is reduced only to the (15S)-nitrolactone (+)-5 and, after subsequent transformations, to (+)-(-S)-15-hexadecanolide ((+)-1), enantiomer of the naturally occurring (-)-1.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19890720523
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