Journal of the Chemical Society. Perkin transactions I p. 1567 - 1575 (1996)
Update date:2022-07-30
Topics:
Muraoka, Osamu
Zheng, Bao-Zhong
Okumura, Kazuhito
Tanabe, Genzoh
Momose, Takefumi
Eugster, Conrad Hans
The transformation of the 'fork head ketone' 3b into the corresponding bicyclic lactone 13 via the Beckmann followed by the Huisgen-White rearrangement is described. Application of the method to a homochiral 2-ethyl-substituted bicyclic ketone (+)-3dα gave efficiently (-)-dihydropalustramic acid (-)-2a, a degradation product from the alkaloid palustrine 1, in good optical yield.
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