Syntheses of Strychnos and Aspidospermatan-Type Alkaloids. 8. Selective Total Syntheses of Mossambine and 14-epi-Mossambine by a Radical Cyclization Reaction(1).
Mossambine (6) was obtained by a six-step reaction sequence from the indoloazepine ester 7. Radical cyclization of the tetracyclic vinyl iodide 12a provided a racemic pentacyclic ketone 16E, which could be converted to either enantiomer by condensation with (S or R)-N,S-dimethyl-S-phenylsulfoximine and selective pyrolysis of the resulting diastereomeric alcohols 18 and 19 or 20 and 21. Selective reductions of the resolved (or racemic) ketone 16E provided mossambine (6) and its hydroxy epimer 17.
Kuehne
Martin E.
ME
Department of Chemistry, University of Vermont, Burlington, Vermont 05405.
Wang
Tiansheng
T
Seraphin
Denis
D