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

Autor:	Conrad Hans Eugster, Genzoh Tanabe, Osamu Muraoka, Takefumi Momose, Bao-Zhong Zheng, Kazuhito Okumura
Rok vydání:	1996
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Ketone Bicyclic molecule Tandem Chemistry Stereochemistry Enantioselective synthesis Molecule Nonane Lactone Baeyer–Villiger oxidation
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :1567-1575
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19960001567
Popis:	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-etyl-substituted bicyclic ketone (+)-3dα gave efficiently (–)-dihydropalustramic acid (–)-2a, a degradation product from the alkaloid palustrine 1, in good optical yield.
Databáze:	OpenAIRE
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