627873-27-2

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 627873-25-0 (1S,5R,6R)-5-Hydroxy-7-(4-methoxy-benzyl)-7-aza-bicyclo[4.1.0]hept-3-en-2-one 
• 627873-18-1 (1aS,3aR,6aS,6bR)-1-(4-Methoxy-benzyl)-5,5-dimethyl-hexahydro-4,6-dioxa-1-aza-cyclopropa[e]inden-2-one 
• 355401-57-9 (3aR,7aS)-6-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-one 

Downstream Products

• 627873-29-4 (1S,3R,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyl)-4-oxa-8-aza-tricyclo[5.1.0.0^3,5]octan-2-one 

Relevant academic research and scientific papers

Use of aziridines for the stereocontrolled synthesis of (-)-LL-C10037α, (+)-MT35214, and (+)-4-epi-MT35214

Strategies for the synthesis of the title compounds have been developed using a diastereoselective aziridination reaction of 4-O-substituted cyclohexenones. Aziridination using a chiral amine permitted resolution of a 4-hydroxycyclohexane derivative, and this resulted in the synthesis of both enantiomers of the title compound. Alternatively, the chiral 4-hydroxycyclohexenone starting material was derived from quinic acid. In both cases stereoselective epoxidation and opening of the aziridine ring with hydrazoic acid afforded the 2-azidocyclohexenone, which was transformed to the 2-acetamido group present in the natural product.

Aziridines as a Protecting and Directing Group. Stereoselective Synthesis of (+)-Bromoxone

(Equation presented) The directing ability of an aziridine group for the epoxidation of adjacent double bonds is demonstrated. The aziridine group is also used to effectively protect a double bond in a cycloenone system for a short synthesis of the title