60216-46-8Relevant academic research and scientific papers
Applications of crotonyldiisopinocampheylboranes in synthesis: Total synthesis of restrictinol
Barrett, Anthony G. M.,Bennett, Adrian J.,Menzer, Stefan,Smith, Marie L.,White, Andrew J. P.,Williams, David J.
, p. 162 - 171 (2007/10/03)
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.
A convenient one-pot synthesis of (E)-silylated conjugated enynes from 1,1-bis(trimethylsilyl)-2-propyne and carbonyl derivatives
Pornet, Jacques,Princet, Bruno,Mevaa, Luc Mbaze,Miginiac, Leone
, p. 2099 - 2111 (2007/10/03)
1,1-Bis(trimethylsilyl)-2-propyne, prepared from propargyltrimethylsilane, was reacted, in the presence of a Lewis acid, with electrophiles (aldehydes, acetals) to afford (E)-silylated conjugated enynes.
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
Argenti,Bellina,Carpita,Rossi,Rossi
, p. 2281 - 2297 (2007/10/02)
(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
Andreini, Bianca Patrizia,Carpita, Adriano,Rossi, Renzo
, p. 5533 - 5534 (2007/10/02)
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.
