Tandem Beckmann and Huisgen-White rearrangement as an alternative to the Baeyer-Villiger oxidation of the bicyclo[3.3.1]nonane system: First asymmetric synthesis of (-)-dihydropalustramic acid. X-Ray molecular structure of 2β-ethyl-9-phenylsulfonyl-9-azabicyclo[3.3.1]nonan-3-one

DOI: 10.1039/P19960001567

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1567 - 1575 (1996)

Update date:2022-07-30

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Authors:

Muraoka, Osamu

Zheng, Bao-Zhong

Okumura, Kazuhito

Tanabe, Genzoh

Momose, Takefumi

Eugster, Conrad Hans

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Article abstract of DOI:10.1039/P19960001567

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.

Full text of DOI:10.1039/P19960001567

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