Davidson James P, Corey E J
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
J Am Chem Soc. 2003 Nov 5;125(44):13486-9. doi: 10.1021/ja0378916.
A concise, enantiospecific synthesis of pseudopteroxazole (3), which had originally been assigned structure 1, has been accomplished starting from S-(-)-limonene. The known cyclohexanone 5 was converted in five steps to the alpha,beta-enone 8 by a modified Robinson annulation. Transformation of 8 to the orthogonally protected amino phenol 11 was accomplished by a new modification of the Wolff-Semmler rearrangement. The synthesis was completed by cationic cyclization to form 14 diastereoselectively and subsequent introduction of the terminal oxazole subunit.
