ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
(+)-Fenchone (3a) was transformed to 6-exo-hydroxy-fenchone (6β-hydroxy-1, 3, 3-trimethyl-nor-bornan-2-one) (1a) and to 5-exo-hydroxy-fenchone 5β-hydroxy-1, 3, 3-trimethyl-nor-bornan-2-one (4a) by the mycelium of Absidia orchidis (Vuill.) Hagem. The structure of the two products was proven by a detailed analysis of the NMR. spectra of the corresponding acetyl derivatives 2a and 5a respectively, and by CrO3-oxidation. 1a yielded the β-diketone 6a, and 4a the diketone 8a. Whereas 8a was stable to alkali 6a was cleaved to the cyclopentane carboxylic acids 7 and 9. - Incubation of ( - )-fenchone (3b) yielded the enantiomeric hydroxylation products 1b and 4b in the same ratio. - ( - )-Isofenchone (11a) was transformed by Absidia orchidis into the two epimers 6-endo-hydroxy-isofenchone (6β-hydroxy-1, 5, 5-trimethyl-nor-bornan-2-one) (12a) and 6-exo-hydroxy-isofenchone (6β-hydroxy-1, 5, 5-trimethyl-nor-bornan-2-one) (10a.) CrO3-oxidation of both 10a and 12a gave the same β-diketone 6a. - (+)-Isofenchone gave the corresponding enantiomeric hydroxy derivatives 10b and 12b on incubation with Absidia orchidis.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19690520622