American Chemical Society
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First Enantiospecific Total Synthesis of the Antitubercular Marine Natural Product Pseudopteroxazole. Revision of Assigned Stereochemistry

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journal contribution
posted on 2003-10-10, 00:00 authored by James 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.