23192-42-9Relevant academic research and scientific papers
Preapration of 7,8,16-trihydroxy-hexadecanoic acid from aleuritic acid and a synthesis of E/Z-7-hexadecen-1,16-olides and hexalure
Tewari, Neera,Rohatgi, Amit,Bhushan, Kumar Hari,Subramanian, G. B. V.
, p. 851 - 855 (2007/10/03)
Both threo/erythro 7,8,16-trihydroxy-hexadecanoic acids have been preapred from threo/erythro 9,10,16-trihydroxy-hexadecanoic acids (aleuritic acid), by interchanging the positions of the terminal carboxyl and hydroxyl groups through steps of appropriate oxidation-reduction on the dithianes obtained from the 16-oxo-9,10-dihydroxy-hexadecanoic acids.Cyclization of the corresponding 9,10-olefin with dibutyl tin oxide furnish E/Z-7-hexadecen-1,16-olides.Preparation of the insect pheromone hexalure is also reported.
Vinylic Organoboranes. 3. Pheromones via Organoboranes. 1. Stereospecific Synthesis of Straight-Chain Z-Monoolefinic Insect Pheromones via Lithium (1-Alkynyl)trialkylborates
Brown, Herbert C.,Wang, Kung K.
, p. 4514 - 4517 (2007/10/02)
Various insect pheromones with straight-chain Z-monoolefinic structures have been prepared from lithium (1-alkynyl)trialkylborates.Treatment of lithium (1-alkynyl)trialkylborates, readily prepared from lithium acetylides and trialkylboranes, with iodine under mild conditions produces the corresponding alkynes in essentially quantitative yield.Monohydroboration of the resultant alkyne with 9-borabicyclononane yields the corresponding (Z)-olefin after protonolysis.The combination of these two reaction sequences provides a general route for the synthesis of (Z)-olefins.The position of the double bond and the carbon-chain length are easily controlled by properly choosing the initial reactants.The incorporation of functional groups is also easily achieved because of the mild reaction conditions and the tolerance of hydroboration to many functional groups.High yield and purity of the products are obtained.
