1989 Volume 109 Issue 12 Pages 887-912
For the purpose of the construction of ring systems, three novel methodologies ; (1) sulfeno-cycloamination, (2) enamine annulation, and (3) intramolecular double Michael reaction, were developed. The usefulness of these methods has been proved by total syntheses of a number of natural products. Indolizidine alkaloids and β-lactam antibiotics were synthesized by application of the sulfeno-cycloamination. Total syntheses of Ipecac alkaloids, Corynanthe alkaloids and Camptotheca alkaloids were accomplished by exploitation of the enamine annulation. Diterpene, Aconitum alkaloid, angular triquinane sesquiterpenes, estrane type steroids, phenanthroindolizidine alkaloid and quinolizidine alkaloid were effectively synthesized by the intramolecular double Michael reaction as the key step.
