Total Synthesis of - -Suaveoline

Abstracted with permission from J. Org. Chem., 1993,58, 661 1993 American Chemical Society 

---

Total Synthesis of Suaveoline (261) via an Intramolecular Diels—Alder Reaction 157... 

Trudell had originally achieved a total synthesis of ( )-suaveoline from ( )-tryptophan and in 1992 Fu et finished a total synthesis of (—)-sua-... 

During the enantiospecihc total synthesis of ajmalin-related alkaloids, (-)-suaveoline and (-)-raumacline, N-debenzylation of the hydrochloride salt of the alkaloids was performed with 10% Pd/C (0.12 mol Pd/mol compound) in absolute EtOH at room temperature and 1 atm of hydrogen for 1 or 2 hours. When this catalytic debenzylation was performed, however, using 10% Pd/C (0.28 mol Pd/mol compound) in MeOH for 5 hours, N-methyl derivatives were produced in good yield (Scheme 4.91).339,340... 

Cloudsdale, I. S. Kluge, A. F. McClure, N. L.J. Org. Chem. 1982, 47, 919—928. Soerens, D. A. Part I. Studies of the Pictet—Spengler Reaction in Aprotic Media. Part 11. Studies Directed toward the Total Synthesis of the Indole Alkaloid Suaveoline University of Wisconsin-Milwaukee Milwaukee, WI, 1978. 

---