944282-79-5Relevant articles and documents
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.