A rapid entry to C-prenylcarbazoles: total synthesis of clausamine C-D, clausevatine D and clausine F.
The key prenylcarbazole precursor 33 was readily assembled from diester 30 by an ester-driven para-Claisen rearrangement followed by selective removal of the ester function. Unusual oxidative cyclization of 33 by m-CPBA resulted in the total synthesis of tetracyclic carbazole natural products 3 and 11.
Jana
Amit Kumar
AK
Department of Chemistry, Indian Institute of Technology, Kharagpur-721302, India.
Mal
Dipakranjan
D
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D010084:Oxidation-Reduction
D000470:Alkaloids; D002227:Carbazoles; C528596:clausamine C; C552078:clausamine D; C528594:clausevatine D; C076712:clausine F