956247-47-5

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 108943-42-6 (S)-(+)-hexane-1,3-diol 

Downstream Products

• 262588-88-5 (3S)-3-(benzyloxy)hexan-1-ol 
• 262588-90-9 8-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-undec-4-yn-6-ol 
• 262588-94-3 6-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-non-2-yn-4-ol 
• 262588-92-1 (S)-8-Benzyloxy-1-(tetrahydro-pyran-2-yloxy)-undec-4-yn-6-ol 
• 262588-91-0 8-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-undec-4-yn-6-ol 
• 262588-89-6 (S)-4-Benzyloxy-tridec-7-yn-6-ol 
• 1035455-07-2 C₁₃H₁₈O₂ 

Relevant academic research and scientific papers

Br?nsted acid promoted intramolecular cyclization of O-alkynyl benzoic acids: Concise total synthesis of exserolide F

Herein we report the stereoselective total synthesis of Exserolide F. The key step involves triflic acid catalyzed highly regioselective intramolecular cyclization of an O-alkynyl benzoic acid derivative to accomplish the core isocoumarin skeleton of the natural product via 6-endo-dig mode of cyclization. The other important steps are: Sharpless asymmetric epoxidation, Barbier propargylation, Sonogashira coupling en route to access the O-alkynyl benzoic acid derivative.

A stereoselective total synthesis of (-)-andrachcinidine via an olefin cross-metathesis protocol

A stereoselective total synthesis of 1-(2S,6R)-6-[(2S)-2-hydroxypentyl]-hexahydro-2-pyridinylacetone, (-)-andrachcinidine is reported. The strategy utilizes olefin cross-metathesis and intramolecular SN2 cyclization as the key steps.

[1,3]-Transfer of chirality during the nicholas reaction in γ-benzyloxy propargylic alcohols

A highly regio- and stereoselective intramolecular [1.5]-hydrogentransfer process is described. Treatment of γ-benzyl-protccted Co 2(CO)6-α,γ-acetylenic diols with BF 3·OEt2 provides bis-homopropargylic alcohols. The reaction occurs within seconds, tolerates a wide range of functionalities, and provides good yields. When the ether group is located at a stereochemically defined carbon atom, the rearrangement occurs with high stereoselectivity, transferring the chirality of the carbinol center to the newly created stereocenter. The cleavage of the benzyloxy group is totally regioselective when additional benzyl ethers are present. The scope and limitations of this novel process in densely substituted substrates are evaluated, and possible competitive reactions and/or stereochemical influences are also described. A mechanism based on a highly ordered chair-like transition state substantiated by a theoretical study is also included.