334705-97-4

Upstream product

• 75658-86-5 (1S,5R)-3-oxabicyclo[3.1.0]hexan-2-one 
• 4606-10-4 allyl diazoacetate 
• 334705-96-3 2-((1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-2-ol 

Downstream Products

• 864382-64-9 (R)-2-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-propionaldehyde 
• 460997-46-0 (4S)-4-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)pentanal 
• 460997-49-3 (1S,3S,4S,7S)-4-hydroxy-7-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-1,3-dimethyl-2-oxooctyl benzoate 
• 460997-44-8 ethyl (E),(4R)-4-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)pent-2-enoate 
• 460997-45-9 ethyl (4S)-4-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)pentanoate 
• 460997-48-2 (1S,3S,4S,7S)-7-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)-4-hydroxy-1,3-dimethyl-2-oxooctyl benzoate 
• 460997-43-7 (2R)-2-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-1-ol 

Relevant academic research and scientific papers

Total synthesis of zincophorin and its methyl ester

A total synthesis of the naturally occurring ionophore zincophorin has been realized. The route features an intramolecular oxymercuration of a cyclopropanemethanol and a Carroll-Claisen rearrangement for the respective elaboration of the C1-C12 and C13-C25 subunits, which have been assembled by using a highly diastereoselective titanium-mediated aldol condensation.

Synthesis of isopropenylcyclopropanes - Revision of the relative configuration of cyclopropyl ketones obtained by 1,3-elimination of γ-epoxy ketones

Efficient stereoselective routes towards isopropenylcyclopropanes have been devised. Secondary cis-isopropenylcyclopropylcarbinols have been obtained either by regio- and stereoselective hydroxy-directed cyclopropanation of the corresponding dienols or from bicyclic cyclopropyl lactones derived from intramolecular cyclopropanation of allylic diazoacetates. Contrary to previous reports, base-induced 1,3-elimination of γ-epoxy ketones has been shown to afford trans-2-(hydroxymethyl)cyclopropyl ketones, and the reactivity of these compounds has been reinvestigated.