80994-68-9

Upstream product

• 99864-98-9 undec-3t-ene-5,7-diyn-2-one 
• 14752-60-4 pentynyl bromide 
• 68267-52-7 pent-2t-en-4-ynoic acid 
• 91060-73-0 (E)-2-decen-4,6-diyn-1-ol 
• 114825-66-0 ethyl (E)-2-decen-4,6-diynoate 
• 627-19-0 1-Pentyne 
• 34501-90-1 (E)-pent-2-en-4-yn-1-al 
• 34501-84-3 (3E)-hex-3-ene-5-yn-2-one 
• 35042-52-5 (E)-2-penten-4-yn-1-ol 
• 99172-22-2 2-methylnona-3,5-diyn-2-ol 
• 10313-06-1 hepta-1,3-diyne 
• 99058-77-2 (E)-dec-2-ene-4,6-diynal 

Downstream Products

• 505-01-1 methyl (Z)-dec-2-ene-4,6-diynoate 
• 3788-06-5 trans-lachnophyllum ester 

Relevant academic research and scientific papers

STEREOCONTROLLED SYNTHESIS OF NATURALLY-OCCURRING POLYACETYLENES CHARACTERIZED BY (E)-1-EN-3-YNE, (E)-1-EN-3,5-DIYNE, (1E,5E)-1,5-DIEN-3-YNE, AND (1E,7E)-1,7-DIEN-3,5-DIYNE MOIETIES

A stereocontrolled synthesis of five naturally-occurring polyacetylenes, i.e. methyl (E)-5-(2-thienyl)-2-penten-4-ynoate, 9, (E)-N-methyl-N-(2-methylpropyl)-2-decen-4,6-diynamide, 10, (E)-1-(3-methyl-2-butenoyloxy)-2-decen-4,6-diyne, 11, (2E,6E)-1-acetoxy-2,6-decadien-4-yne, 12, and (2E,8E)-1-acetoxy-2,8-decadien-4,6-diyne, 13, is reported.The flexible strategy involves palladium(0)-copper(I) catalyzed coupling reactions to construct the carbon skeleton of the target molecules and to prepare an important C5 building block, i.e. (E)-2-penten-4-yn-1-ol, 21.This compound is also an useful intermediate to lipoxins A and B.A highly diastereoselective palladium-catalyzed carbon-carbon bond forming reaction, recently developed in our laboratory, has been used in a key synthetic step to compound 12.