Total synthesis, stereochemistry, and lithium–ammonia reduction of (±)-4-demethylaristolone and (±)-5-epi-4-demethylaristolone
- 1 December 1969
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 47 (23) , 4299-4306
- https://doi.org/10.1139/v69-713
Abstract
The total synthesis of (±)-4-demethylaristolone (14) and its epimer, (±)-5-epi-4-demethylaristolone (15) is described. The key step of this synthesis involves the intramolecular cyclization of the olefinic diazoketone 12, which produces the two epimers, 14 and 15, in a ratio of approximately 2:1, respectively. The stereochemistry of the two epimers is unambiguously determined. It is observed that the lithium–ammonia reduction of 14 gives a dihydro derivative 16 containing trans-fused six-membered rings, while, interestingly, a similar reduction of 15 affords the corresponding cis-fused decalone system 26.Keywords
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