Prasad, Pavirayani R and Chandrakumar, Appayee (2007) Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine [Jaspine B]. In: Journal of Organic Chemistry, 72 (16). pp. 6312-6315.
123.pdf - Published Version
Restricted to Registered users only
Download (89Kb) | Request a copy
A practical stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) was achieved in 48% overall yield from D-(-)-tartaric acid. Key features of the sequence include the diastereoselective formation of a tetrol with three contiguous chiral centers, which was further elaborated to pachastrissamine. The synthetic route is operationally simple, diastereoselective and is amenable for the synthesis of a number of analogues of pachastrissamine.
|Item Type:||Journal Article|
|Additional Information:||Copyright of this article belongs to American Chemical Society.|
|Keywords:||asymmetric-synthesis;enantioselective synthesis; enantiospecific synthesis;l-(+)-tartaric acid;marine sponge; phytosphingosine;enantiomers;derivatives;lactones.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||30 Apr 2010 08:57|
|Last Modified:||19 Sep 2010 06:01|
Actions (login required)