First total syntheses of dihydroflustramine C and flustramine E, alkaloids from the marine bryozoan Flustra foliacea. Morales-Ríos Martha S., Suárez-Castillo Oscar R., Joseph-Nathan P. DOI: http://dx.doi.org/10.1016/S0040-4020(02)00011-X
We have developed a simple and practical method for providing the common tricyclic skeleton of physostigmine type alkaloids, and demonstrated its utility for indole alkaloid synthesis. Thus, we achieved the firsttotalsyntheses of ()-dihydroflustramine C and ()-flustramine E, as well as the totalsyntheses of their debromoanalogues from the corresponding 2-hydroxyindolenines in five steps with 31, 27, 39 and 23% overall yields, respectively. The structures of some intermediates were confirmed by single crystal X-ray diffraction analyses.