Issue 31, 2016

The first total synthesis of potent antitumoral (±)-mafaicheenamine A, unnatural 6-fluoromafaicheenamine A and expedient synthesis of clausine E

Abstract

The first total synthesis of potent antitumoral mafaicheenamine A (1) and its unnatural analogue, 6-fluoromafaicheenamine A (2) have been accomplished. An expedient synthesis of clausine E, a key intermediate in the course of synthesis of 1 and 2, was achieved in three steps from commercially available methyl 4-amino-3-(benzyloxy)benzoate (10) by copper-catalyzed N-arylation with aryllead triacetate, followed by cyclodehydrogenation of the resultant diarylamine under palladium(II) acetate catalysis. Moreover, palladium-catalyzed O-prenylation of clausine E and subsequent o-Claisen rearrangement under microwave irradiation rendered the advanced intermediate, C-prenylated phenol, which was eventually subjected to oxidative cyclization to construct the dihydroisocoumarin unit, leading to the synthesis of 1 and 2 in 12% and 15% overall yield, respectively, from 10.

Graphical abstract: The first total synthesis of potent antitumoral (±)-mafaicheenamine A, unnatural 6-fluoromafaicheenamine A and expedient synthesis of clausine E

Supplementary files

Article information

Article type
Paper
Submitted
03 Feb 2016
Accepted
02 Mar 2016
First published
03 Mar 2016

RSC Adv., 2016,6, 26104-26110

The first total synthesis of potent antitumoral (±)-mafaicheenamine A, unnatural 6-fluoromafaicheenamine A and expedient synthesis of clausine E

Y. Abbas, M. Mansha and N. Ullah, RSC Adv., 2016, 6, 26104 DOI: 10.1039/C6RA03242G

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