612481-26-2Relevant academic research and scientific papers
Synthesis of the otteliones A and B: Use of a cyclopropyl group as both a steric shield and a vinyl equivalent
Clive, Derrick L. J.,Liu, Dazhan
, p. 3738 - 3740 (2007)
(Chemical Equation Presented) To A and B: The extremely powerful antitumor agents ottelione A and B have been synthesized from D-ribose. Key steps in the synthesis involve the use of a cyclopropane unit fused onto a five-membered ring to control the stere
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.
Enantioselective total syntheses of (+)- and (-)-ottelione A and (+)- and (-)-ottelione B. Absolute configuration of the novel, biologically active natural products
Mehta, Goverdhan,Islam, Kabirul
, p. 6733 - 6736 (2007/10/03)
Following our recent total synthesis of the biologically potent natural products otteliones A and B in racemic form, we have now accomplished the total synthesis of both the enantiomers of otteliones A and B through an enantiodivergent strategy emanating from the readily available Diels-Alder adduct of cyclopentadiene and p-benzoquinone. These endeavors have led to the elucidation of the absolute configuration of naturally occurring otteliones A and B.
