ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
In a highly diastereoselective fashion novel 11β, 17β-diaryl steroids 17 and 18 were synthesized via Birch-type reduction [1] of styrylic precursors 11 and 15. Both precursors were readily available by Suzuki-type coupling reactions [2] of aromatic boronic acids [3] and the corresoponding enol triflates 6, 10, and 14. Regioselective 17-enol triflate formation in presence of a 11-keto function could be demonstrated in case of steroid 5. The remarkably high degree of stereo-selectivity observed parallels results from the natural series [4] and demonstrated a broader applicability of such single electron transfer reductions in stereoselective transformations on the steroid skeleton.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19973390164
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