155795-29-2

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 146747-65-1 benzyl 3-oxo-9-azabicyclo<3.3.1>nonanane-9-carboxylate 
• 146747-65-1 (1R,5S)-3-Oxo-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester 

Downstream Products

• 155795-30-5 methyl (1S,5R)-(+)-9-(benzyloxycarbonyl)-3-hydroxy-9-azabicyclo<3.3.1>non-2-ene-2-carboxylate 
• 155897-12-4 (+)-benzyl 2β-ethyl-3-oxo-9-azabicyclo<3.3.1>nonane-9-carboxylate 
• 155795-31-6 methyl (1S,2R,5R)-(+)-9-(benzyloxycarbonyl)-2-ethyl-3-oxo-9-azabicyclo<3.3.1>nonane-2-carboxylate 
• 155795-32-7 methyl (2R,6R)-(-)-1-benzyloxycarbonyl-6-propylpiperidine-2-acetate 

Relevant academic research and scientific papers

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

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.

The Norrish Type I Photo-cleavage of (+)-2β-Ethyl-9-azabicyclononan-3-one: A Short, Enantioselective Formal Synthesis of (-)-Indolizidine 223AB

The enantioselective alkylation of the "fork head ketone" (1) followed by the Norrish Type I photo-cleavage provided the short enantioselective synthesis of (-)-indolizidine 223 AB (4).