Chemistry of Natural Compounds p. 372 - 374 (1985)
Update date:2022-08-17
Topics:
Odinokov, V. N.
Ishmuratov, G. Yu.
Balezina, G. G.
Tolstikov, G. A.
A new route is proposed for the synthesis of dodec-8E-enyl and dodec-8Z-enyl acetates which is based on the reaction of the Grignard reagent from the readily accessible 1-bromo-5-(1-ethoxyethoxy)pentane with 1-bromohept-3-yne - the bromide obtained from product of the β-hydroxyethylation of pent-1-yne with 2-chloroethylvinyl ether, hept-3-yn-1-ol, by a double decomposition reaction of its tosylate with lithium bromide.The key synthon - dodec-8-yn-1-ol - was converted with the aid of sodium in liquid ammonia into the stereochemical individual dodec-8E-enol, while its reduction with the aid of 9-borabicyclo<3.3.1>nonane (BBN) gave the stereoisomeric alcohol exclusively with the Z configuration, as followed from the results of capillary GLC and the IR spectra of the corresponding acetates.The PMR spectra of the compounds synthesized are also given.
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