764-58-9

Upstream product

• 93336-35-7 4-ethylsulfanyl-hepta-2,3-diene 
• 123-72-8 butyraldehyde 
• 106-96-7 propargyl bromide 
• 60216-46-8 trans-1-Trimethylsilylhept-3-en-1-yn 
• 31849-76-0 pentenyl bromide 
• 109-67-1 1-penten 
• 60468-23-7 (E)/(Z)-1-bromo-1-pentene 

Downstream Products

• 70737-20-1 (cis-2-bromo-vinyl)-trimethyl-silane 
• 126262-21-3 (1E,5E)-1-trimethylsilyl-1,5-nonadien-3-yne 
• 29576-70-3 (2E,6E)-1-acetoxy-2,6-decadien-4-yne 
• 29576-70-3 Acetic acid (2E,6Z)-deca-2,6-dien-4-ynyl ester 
• 224967-47-9 (+)-(2R,3R,5R)-2-hydroxymethyl-3-(1,3-heptadienyl)-5-(tert-butyldimethylsiloxy)cyclohexanone 
• 128856-71-3 (2R,3R,5R)-2,3-bis-(O-trimethylsilyl)-2,3-dihydroxy-5-(1',3'-E,E-1'-heptadienyl)-cyclohexanone 
• 140224-89-1 3-hepta-1,3-dienyl-5,6-dihydroxy-2-hydroxymethylcyclohexanone 
• 251959-53-2 (2R,3S,5R,6R)-3-((1E,3E)-Hepta-1,3-dienyl)-2-hydroxymethyl-5,6-bis-trimethylsilanyloxy-cyclohexanone 
• 1002-94-4 (10Z,12E)-hexadecadien-1-ol 
• 864-40-4 Hexadecadien-(10c,12t)-yl-⁽¹⁾-4'-nitro-azobenzol-carbonsaeure-⁽⁴⁾-ester 
• 186900-40-3 penihydrone 
• 186900-37-8 (5S,6R)-5-((1E,3E)-hepta-1,3-dienyl)-6-hydroxymethyl-cyclohex-2-enone 

Relevant academic research and scientific papers

Applications of crotonyldiisopinocampheylboranes in synthesis: Total synthesis of restrictinol

The total synthesis of restrictinol, the hydrolysis product of the antifungal natural product restricticin, starting from commercially available methyl (S)-(+)-3-hydroxy-2-methylpropionate is described. Key stages in the strategy involved (i) the use of Brown's allylboration chemistry to construct an acyclic intermediate bearing three of the four stereogenic centers of the natural product, (ii) formation of a C-glycosidic vinyl iodide, and (iii) introduction of the triene side chain via a Suzuki coupling reaction.

Trail-following in termites: Stereoselective syntheses of (Z)-3-Dodecen- 1-OL, (3Z,6Z)-3,6-Dodecadien-1-OL and (3Z,6Z,8E)-3,6,8-dodecatrien-1-OL

(Z)-3-Dodecen-1-ol (4), a candidate trail-following semiochemical for several termite species, was synthetized by (Z)-stereoselective reduction of 3-dodecyn-1-ol (8). (3Z,6Z)-3,6-Dodecadien-1-ol (6), which is a structural analogue of 4, was prepared by a reaction sequence in which the key step was the cross-coupling between 5-(tert-butyldimethylsilyloxy)-2-pentyn-1-yl p- toluene-sulfonate (11) and 1-heptyne (12), in the presence of Cul, NaI and K2CO3. Finally, (3Z,6Z,8EZ)-3,6,8-dodecatrien-1-ol (3), which is a non- species-specific trail-following pheromone of termites, was prepared by a convergent synthesis in which compound 11 and (E)-3-hepten-1-yne (18) were used as key intermediates.

DIASTEREOSELECTIVE SYNTHESIS OF (E)-1-TRIMETHYLSILYL-3-EN-1-YNES BY PALLADIUM-CATALYZED CROSS-COUPLING REACTION BETWEEN TRIMETHYLSILYLETHYNYLZINC CHLORIDE AND STEREOISOMERIC MIXTURES OF 1-BROMO-1-ALKENES

In the stereospecific palladium-catalyzed cross-coupling reaction of trimethylsilylethynylzinc chloride, (E)-1-bromo-1-alkenes react preferentially in the presence of the corresponding (Z)-stereoisomers.