posted on 2003-10-10, 00:00authored byJames P. Davidson, E. J. Corey
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 α,β-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.