ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The diastereoisomeric (+)-[1,8-14C]-(1'R,6R, S)-α-bisabolol (2a) and (-)-[1,8-14C]-(1′S, 6R, S)-α-bisabolol (2b) were synthesized by reaction of the Grignard compound of [1,6-14C]-5-bromo-2-methyl-2-pentene (12) with (+)-(R)- and (-)-(S)-4-acetyl-1-methyl-1-cyclohexene, (6a) and (6b) respectively. For the preparation of compound 12, cyclopropyl methyl ketone was treated with [14C]-methyl magnesium iodide to form the carbinol 11, which was cleaved by HBr. Compounds 6a and 6b were synthesized from (+)-(R)- and (-)-(S)-limonene, (4a) and (4b), via the derivatives 5a, 6a and 5b, 6b respectively. - This synthesis established the absolute configuration at C(1′) of the natural α-bisabolols: (R) for (+)-α-bisabolol and (S) for (-)-α-bisabolol. - Feeding experiments with cultures of Myrothecium roridum and radioactive (+)-(1′R, 6R, S)- and (-)-(1′S, 6R, S)-α-bisabolol (2a) and (2b) gave negative results. These findings indicate that bisabolane derivatives are not intermediates in the biosynthesis of verrucarol (3).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19750580418
