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Communication | Regular issue | Vol 36, No. 1, 1993, pp.7-11
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6176
The Tandem Beckmann and Huisgen-White Rearrangement as an Alternative to the Baeyer-Villiger Oxidation of the 9-Azabicyclo[3.3.1]nonan-3-one System: A Facile Route to (±)-Dihydropalustramic Acid

Takefumi Momose,* Kazuhito Okumura, Hisayuki Tsujimori, Kaori Inokawa, Genzoh Tanabe, Osamu Muraoka,* Yoh Sasaki, and Conrad Hans Eugster

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan


The transformation of the "fork head ketone" (1) into the corresponding bicyclic lactone (4) via the Beckmann followed by the Huisgen-White Rearrangement is described. An α-ethyl-substituted bicyclic ketone (5) was converted efficiently to dihydropalustramic acid (6), a degradation product from the alkaloid palustrine.