219498-10-9Relevant academic research and scientific papers
A direct and efficient stereocontrolled synthetic route to the pseudopterosins, potent marine antiinflammatory agents
Corey,Lazerwith, Scott E.
, p. 12777 - 12782 (2007/10/03)
Described herein is a new synthetic route to pseudopterosin aglycone (3), a key intermediate for the synthesis of a group of antiinflammatory natural products including pseudopterosin A (1) and E (2). The pathway of synthesis starts with the abundant and inexpensive (S)-(-)-limonene and its long-known cyclic hydroboration product (4) and leads to the chiral hydroxy ketone 6. Conversion of 6 to 10 followed by a novel aromatic annulation produced 15 which underwent a highly diastereoselective cyclization to afford the protected pseudopterosin aglycone 16. The naturally occurring pseudopterosins such as 1 and 2 are readily available from this key intermediate.
