Transformation of carboxylic acid esters into 2-substituted allyl halides through tertiary cyclopropyl sulfonates. Application in the synthesis of (±)-ipsenol and (±)-ipsdienol, components of Ips typographus spark beetle pheromone

Article abstract of DOI:10.1134/S1070428006040038

Cyclopropanation of the ester group in ethyl 3-chloropropanoate and subsequent cleavage of the three-membered carbocycle in intermediate 1-(2-chloroethyl)cyclopropyl methanesulfonate gave 2-bromomethyl-4-chlorobut-1- ene, and the latter was used as key intermediate in the synthesis of racemic ipsenol and ipsdienol which are components of Ips typographus L. European spruce spark beetle pheromone. Pleiades Publishing, Inc., 2006.

Full text of DOI:10.1134/S1070428006040038

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WUXPꢄꢃ ꢄꢃFP ꢒꢃꢈꢇꢇꢇꢄꢃꢂꢑꢀꢇꢌꢃ +ꢃ105ꢃVSHFWUXPꢄꢃ ꢄꢃSSPꢒꢃ
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E ꢃ ꢃꢀꢃ+]ꢋꢄꢃꢅꢌꢇꢅꢃWꢃꢊꢅ+ꢄꢃEꢃ ꢃꢎꢃ+]ꢋꢄꢃꢈꢌꢑꢆ±ꢈꢌꢑꢑꢃPꢃꢊꢅ+ꢋꢄꢃ
ꢈꢌꢎꢀ±ꢈꢌꢏꢈꢃPꢃꢊꢂ+ꢋꢄꢃꢀꢌꢁꢑ±ꢀꢌꢁꢁꢃPꢃꢊꢅ+ꢋꢌꢃ &ꢃ105ꢃVSHFꢉ
WUXPꢄꢃ ꢄꢃSSPꢒꢃꢅꢅꢌꢆꢀꢄꢃꢅꢈꢌꢈꢑꢄꢃꢅꢀꢌꢑꢅꢄꢃꢈꢏꢌꢏꢈꢄꢃꢀꢅꢌꢇꢂꢄꢃꢀꢀꢌꢎꢅꢄꢃ
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WHWUDK\GURꢂꢁ+ꢂS\UDQꢀꢄ,;ꢅꢃꢃ<LHOGꢃꢈꢌꢀꢆꢃJꢃꢊꢁꢑHꢋꢌꢃ,5ꢃ
ꢀꢑꢌꢈꢀꢄꢃꢑꢎꢌꢂꢈꢄꢃꢂꢂꢀꢌꢎꢏꢄꢃꢂꢀꢅꢌꢎꢂꢌꢃ)RXQGꢄꢃHꢒꢃ&ꢃꢑꢈꢌꢂꢇꢍꢃꢃ VSHFWUXPꢄꢃ ꢄꢃFP ꢒꢃꢂꢑꢀꢇꢌꢃ +ꢃ105ꢃVSHFWUXPꢄꢃ ꢄꢃSSPꢒꢃ
ꢆꢌꢏꢏꢃWꢃꢊꢈ+ꢄꢃEꢃ ꢃꢑꢃ+]ꢋꢄꢃꢆꢌꢏꢁꢃWꢃꢊꢈ+ꢄꢃEꢃ ꢃꢑꢃ+]ꢋꢄꢃꢂꢌꢅꢂ±ꢃ
ꢂꢌꢅꢁꢃPꢃꢊꢂ+ꢋꢄꢃꢂꢌꢈꢅ±ꢂꢌꢀꢂꢃPꢃꢊꢆꢌꢇ+ꢋꢄꢃꢂꢌꢀꢈ±ꢂꢌꢇꢎꢃPꢃꢊꢀꢌꢇ+ꢋꢄꢃ
ꢂꢌꢑꢆ±ꢂꢌꢏꢎꢃPꢃꢊꢈ+ꢋꢄꢃꢅꢌꢂꢈꢃGꢌGꢃꢊꢆꢌꢇ+ꢄꢃE ꢃ ꢃꢂꢀꢄꢃE ꢃ ꢃꢑꢃ+]ꢋꢄꢃ
ꢅꢌꢅꢂ±ꢅꢌꢅꢁꢃPꢃꢊꢂ+ꢋꢄꢃꢅꢌꢀꢂꢃGꢌGꢃꢊꢆꢌꢇ+ꢄꢃE ꢃ ꢃꢂꢀꢄꢃE ꢃ ꢃꢑꢃ+]ꢋꢄꢃ
ꢅꢌꢇꢆꢃWꢃꢊꢂ+ꢄꢃEꢃ ꢃꢎꢃ+]ꢋꢄꢃꢅꢌꢇꢀꢃWꢃꢊꢂ+ꢄꢃEꢃ ꢃꢎꢃ+]ꢋꢄꢃꢈꢌꢀꢅ±ꢃ
ꢈꢌꢇꢅꢃ Pꢃ ꢊꢂ+ꢋꢄꢃ ꢈꢌꢑꢂꢃWꢃꢊꢂ+ꢄꢃEꢃ ꢃ ꢎꢃ +]ꢋꢄꢃ ꢈ ꢌꢑꢀꢃ Wꢃ ꢊꢂ+ꢄꢃEꢃ ꢃꢃ
ꢎꢃ+]ꢋꢄꢃꢈꢌꢎꢈ±ꢈꢌꢁꢀꢃPꢃꢊꢅ+ꢋꢄꢃꢀꢌꢑꢆ±ꢀꢌꢑꢎꢃPꢃꢊꢂ+ꢋꢄꢃꢀꢌꢏꢑ±ꢃ
ꢀꢌꢏꢁꢃPꢃꢊꢂ+ꢋꢄꢃꢀꢌꢁꢆꢃVꢃꢊꢂ+ꢋꢌꢃꢃ
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ꢁꢂꢄꢁꢂ&KORURHWK\OꢅꢂꢋꢂPHWK\OKHSWDꢂꢈꢆꢌꢂGLHQꢂꢊꢂROꢃ
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VSHFWUXPꢄꢃ ꢄꢃFP ꢒꢃꢈꢑꢂꢇꢄꢃꢂꢑꢇꢇꢌꢃ +ꢃ105ꢃVSHFWUXPꢄꢃ ꢄꢃ
SSPꢒꢃꢂꢌꢑꢈꢃVꢃꢊꢂ+ꢋꢄꢃꢂꢌꢑꢁꢃGꢃꢊꢈ+ꢄꢃEꢃ ꢃꢂꢃ+]ꢋꢄꢃꢂꢌꢎꢅꢃGꢃꢊꢈ+ꢄꢃꢃ
Eꢃ ꢃꢂꢃ+]ꢋꢄꢃꢅꢌꢂꢑ±ꢅꢌꢈꢆꢃPꢃꢊꢅ+ꢋꢄꢃꢅꢌꢇꢈꢃWꢃꢊꢅ+ꢄꢃEꢃ ꢃꢎꢃ+]ꢋꢄꢃ
ꢈꢌꢑꢈꢃWꢃꢊꢅ+ꢄꢃEꢃ ꢃꢎꢃ+]ꢋꢄꢃꢀꢌꢀꢏꢃWꢌGꢃꢊꢂ+ꢄꢃE ꢃ ꢃꢏꢄꢃE ꢃ ꢃꢇꢃ+]ꢋꢄꢃ
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ꢊꢂ+ꢋꢌꢃ &ꢃ 105ꢃ VSHFWUXPꢄꢃ ꢄꢃ SSPꢒꢃ ꢂꢏꢌꢂꢅꢄꢃ ꢅꢇꢌꢇꢏꢄꢃ
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ꢄꢃSSPꢒꢃꢂꢌꢀꢇ±ꢂꢌꢇꢁꢃPꢃꢊꢀ+ꢋꢄꢃꢂꢌꢑꢅ±ꢂꢌꢁꢆꢃPꢃꢊꢏ+ꢋꢄꢃꢅꢌꢂꢀꢃGꢌGꢃ
ꢊꢆꢌꢇ+ꢄꢃE ꢃ ꢃꢂꢀꢄꢃE ꢃ ꢃꢑꢃ+]ꢋꢄꢃꢅꢌꢂꢁꢃGꢌGꢃꢊꢆꢌꢇ+ꢄꢃE ꢃ ꢃꢂꢀꢄꢃE ꢃ ꢃ
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ꢊꢂ+ꢄꢃEꢃ ꢃꢎꢃ+]ꢋꢄꢃꢈꢌꢀꢂ±ꢈꢌꢀꢁꢃPꢃꢊꢂ+ꢋꢄꢃꢈꢌꢑꢆꢃWꢃꢊꢂ+ꢄꢃEꢃ ꢃꢃ
ꢎꢃ+]ꢋꢄꢃꢈꢌꢑꢈꢃWꢃꢊꢂ+ꢄꢃEꢃ ꢃꢎꢃ+]ꢋꢄꢃꢈꢌꢏꢂ±ꢈꢌꢏꢁꢃPꢃꢊꢂ+ꢋꢄꢃꢀꢌꢈꢁ±
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