476487-41-9Relevant academic research and scientific papers
A short synthetic route to the core structures of otteliones A and B
Clive, Derrick L. J.,Liu, Dazhan
, p. 5305 - 5307 (2005)
Conjugate addition of the cuprate derived from 2-lithio-2,3-butadiene to 1-cylopentenecarbaldehyde, reaction with vinylmagnesium bromide, ring closing metathesis, and oxidation gives the cis-ring fused core of the anticancer agent ottelione A. Epimerization of the initial conjugate addition product and application of the same reactions as used for the ottelione A core, give the trans-ring fused core of ottelione B.
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.
Synthesis of the bicyclic dienone core of the antitumor agent ottelione B
Clive, Derrick L. J.,Fletcher, Stephen P.
, p. 1940 - 1941 (2007/10/03)
The intramolecular Diels-Alder adduct 12 was converted via dimesylate 20 into dienone 7, which represents the unusual, and apparently quite stable, core of the antitumor agent ottelione B (1).
