Hertweck, Christian published the artcileTandem Reduction-Chloroallylboration of Esters: Asymmetric Synthesis of Lamoxirene, the Spermatozoid Releasing and Attracting Pheromone of the Laminariales (Phaeophyceae), Product Details of C21H37BO, the publication is Journal of Organic Chemistry (2000), 65(8), 2458-2463, database is CAplus and MEDLINE.
Asym. synthesis of all four stereoisomers of lamoxirene (cis-2-cyclohepta-2,5-diene-3-vinyloxirane), the spermatozoid-releasing and -attracting pheromone of the Laminariales (Phaeophyceae), is reported. Chiral Et cyclohepta-2,5-diene carboxylates, prepared by a divinylcyclopropane Cope rearrangement, were effectively alkylated by means of a novel tandem DIBAL-H reduction/asym. α-chloroallylboration using (Z)-γ-chloroallyldiisopinocampheylboranes. The ensuing syn-α-chlorohydrins were transformed into the corresponding vinyloxiranes with DBU, providing all four isomers of the pheromone in good chem. and excellent optical yield (90-97% ee). Spermatozoid-release assays were conducted with the sympatrically growing species L. digitata, L. hyperborea, and L. saccharina and established I as the most active isomer in all cases.
Journal of Organic Chemistry published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Product Details of C21H37BO.
Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem