Asymmetric total synthesis of (−)-lingzhiol via a Rh-catalysed [3+2] cycloaddition

Synthesis of triazole-linked morpholino oligonucleotides via Cu catalysed cycloaddition†

Enantioselective formal synthesis of (-)-englerin A via a Rh-catalyzed [4 + 3] cycloaddition reaction.

An enantioselective formal synthesis of (-)-englerin A (1) is reported. Key to the strategy is a Rh-catalyzed [4 + 3] cycloaddition reaction between furan 10 and diazo ester 11 that, following an intramolecular aldol condensation, produces the tricyclic scaffold of englerin. This strategy also provides a rapid, efficient, and stereoselective access to the biologically significant core motif of ...

Asymmetric Total Synthesis of (-)-Englerin A through Catalytic Diastereo- and Enantioselective Carbonyl Ylide Cycloaddition.

An asymmetric total synthesis of the guaiane sesquiterpene (-)-englerin A, a potent and selective inhibitor of the growth of renal cancer cell lines, was accomplished. The basis of the approach is a highly diastereo- and enantioselective carbonyl ylide cycloaddition with an ethyl vinyl ether dipolarophile under catalysis by dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], [Rh2...

Asymmetric total synthesis of (+)-fumimycin via 1,2-addition to ketimines.

The first asymmetric total synthesis of fumimycin was accomplished. As a key step, a 1,2-addition of methyl Grignard reagents to ketimines with quinine as additive was employed. The absolute configuration of (+)-fumimycin was determined by CD-spectroscopy combined with time-dependent density functional calculations.

A convergent rhodium-catalysed asymmetric synthesis of tetrahydroquinolines.

Rh-catalysed conjugate additions of 2-aminophenyl boronic acid derivatives were exploited in diastereoselective and asymmetric syntheses of tetrahydroquinolines. In both cases, combinatorial variation of the substitution of the tetrahydroquinoline ring system was possible.