1.
Org Lett
; 20(21): 6668-6672, 2018 11 02.
Article
in English
| MEDLINE
| ID: mdl-30350650
ABSTRACT
A strategy toward the synthesis of trans-4,5-diaminocyclopent-2-enones is described. This core motif is embedded in the marine sponge derived alkaloids agelamadin B and nagelamide J. A variety of 2-substituted trans-4,5-diaminocyclopent-2-enones were synthesized in good to quantitative yields using lanthanide(III) catalysis. The products were formed exclusively as the trans-diastereomers via a mechanism in which the C4-C5 bond formation occurs through a 4π-conrotatory electrocyclization. The precursor 3-substituted furfurals can be readily accessed using palladium(0)-catalyzed cross-coupling between 3-bromofurfural and boronic acids, trifluoroborate salts, or alkynes.