14523-89-8Relevant articles and documents
Addition of Chloroprene Grignards to Aromatic Aldehydes: Synthesis of Homoallenyl Alcohols
Geissler, Arne G. A.,Breit, Bernhard
supporting information, p. 2621 - 2625 (2021/04/12)
A general procedure for the one-pot synthesis of racemic homoallenyl alcohols from the corresponding aldehyde and chloroprene-derived Grignards is described. Employing bis[2-dimethylaminoethyl]ether (BDMAEE) as an additive at low temperatures shifts the selectivity of the chloroprene Grignard addition to aldehydes such that it is almost exclusive toward allene formation. In a set of follow-up experiments, simple and more elaborate methods for further derivatization have been demonstrated, allowing quick access to more complex structures.
Thermal ring opening of 1,1-dibromo and 1-bromo-2- chloromethylcyclopropanes: Observation of a formal debromochlorination
Sydnes, Leiv K.,Alnes, Karl F. S.,Pettersen, Anita,Brinker, Udo H.
experimental part, p. 479 - 483 (2010/06/16)
When the title compounds are thermolyzed in the gas phase under vacuum or in hot quinoline, several products are formed. A predominant product in all cases is a chlorine-free buta-1,3-diene which has been formed by formal debromochlorination, a reaction n
Synthesis of the potent anticancer agents ottelione A and ottelione B in both racemic and natural optically pure forms
Clive, Derrick L. J.,Liu, Dazhan
, p. 3078 - 3087 (2008/09/19)
(Chemical Equation Presented) The powerful antitumor agents ottelione A and B were synthesized in racemic form by a method that relies on selective ring closing metathesis. Optically pure natural (+)-ottelione A was then made from D-ribose, via an α-keto cyclopropane. A key feature of the route is that the cyclopropyl group controls the stereochemistry in the attachment of the ArCH2 unit and is then converted by the action of SmI2 into a vinyl group, so that the substituents on the resulting five-membered ring have the required trans relationship. Epimerization of an intermediate gave access by the same method to the trans ring fused isomer (-)-ottelione B.