First enantiospecific total synthesis of the antitubercular marine natural product pseudopteroxazole. Revision of assigned stereochemistry.
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.
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
James P
JP
Davidson
E J
EJ
Corey
D000995:Antitubercular Agents / Q000138:chemical synthesis; D003500:Cyclization; D053138:Cyclohexenes; D004224:Diterpenes / Q000138:chemical synthesis*; D000077222:Limonene; D010080:Oxazoles / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry
D000995:Antitubercular Agents; D053138:Cyclohexenes; D004224:Diterpenes; D010080:Oxazoles; D013729:Terpenes; C433836:pseudopteroxazole; D000077222:Limonene