856865-43-5

Upstream product

• 928-95-0 (E)-2-Hexen-1-ol 
• 821-41-0 5-Hexen-1-ol 
• 544-12-7 3-hexen-1-ol 
• 5467-74-3 4-Bromophenylboronic acid 
• 66-25-1 hexanal 
• 6725-74-2 1-bromo-4-(cyclopent-1-en-1-yl)benzene 
• 1357255-87-8 (2RS,6R)-2-hydroxy-6-(4-bromophenyl)tetrahydropyran 
• 1357255-86-7 5-(4-bromophenyl)-5-oxopentanal 
• 1357256-06-4 C₁₂H₁₅BrO 

Relevant academic research and scientific papers

Multicatalytic approach to one-pot stereoselective synthesis of secondary benzylic alcohols

One-pot procedures bear the potential to rapidly build up molecular complexity without isolation and purification of consecutive intermediates. Here, we report multicatalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities (typically >95:5 er) under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Prochiral allylic alcohols can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er, >20:1 dr).

Reversing the reactivity of carbonyl functions with phosphonium salts: Enantioselective total synthesis of (+)-centrolobine

Step saver: Carbonyl groups with lower reactivities can be transformed in the presence of more reactive ones by treatment with PPh3 (or PEt3) and TMSOTf prior to the reaction (see scheme; TMS=trimethylsilyl, Tf=trifluoromethanesulfonyl). This methodology can be applied to reduction and alkylation reactions, and enabled the short asymmetric total synthesis of (+)-centrolobine with the highest overall yield reported to date.

EP2 RECEPTOR AGONISTS

A compound selected from Formula (iv) or Formula (iii); (iv) (1R,2S)-2[4-1(S)-hydroxyhexyl)phenyl]-5-oxo-cyclopentaneheptanoic acid [RSS] or (iii) (1R,2S)-2[4-1(R)-hydroxyhexyl)phenyl]-5-oxo-cyclopentaneheptanoic acid [RSR] or a salt, solvate, chemically protected form or prodrug thereof, and its use in treating conditions alleviated by agonism of an EP2 receptor.