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.
Davidson
James P
JP
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Corey
E J
EJ
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