In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Pheromone synthesis. XXIV. Synthesis of optically active forms of ipsdienol and ipsenol. The pheromone components of Ips bark beetles, published in 1979, which mentions a compound: 58081-05-3, mainly applied to ipsdienol ipsenol pheromone chiral preparation; Ips terpene pheromone, Safety of (R)-4-Hydroxydihydrofuran-2(3H)-one.
(R)-(-)- And (S)-(+)-ipsdienol (I) [(R)-(-)- and (S)-(+)-Me2C:CH(OH)CH2C(:CH2)CH:CH2, resp.] were prepared from (R)-(+)-glyceraldehyde acetonide and (R)-(+)-malic acid, resp., via the intermediate epoxide II and its enantiomer, resp. I is the naturally occurring form of this pheromone. Treating (S)- and (R)-isobutylethylene oxide with CH2:C(MgCl)CH:CH2 gave 32 and 50% (S)-(-)- and (R)-(+)-Me2CHCH2CH(OH)CH2C(:CH2)CH:CH2, resp.
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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem