ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The ‘naked sugar’ (+)-(1R,2R4R)-2-endo-cyano-7-oxabicyclo[2.2.1]hept-5-sn-2-exo-yl acetate ((+)-4) was converted (7 steps, 45% overall) with high stereoselectivity into (-)-(4R,5S,6R)-4,5,6-tris{[(tert-butyl)dimethylsilyl]oxy}cyclohex-2-en-1-one ((-)-11). Reduction of (-)-1 with NaBH4- CeCl3 · 7 H2O, followed by deprotection of the silyl ether moieties gave (+)-conduritol F ((+)-1; 47%) whose characteristics were identical to those of natural (+)-leucanthemitol. Reduction of (-)-11 with DIBAH, followed by deprotection of the silyl ether moiety led to (-)-conduritol B ((-)-3; 51 %).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19900730118