Chemistry of cyclic tautomers of tryptophan: Formation of a quaternary center at C3a and total synthesis of the marine alkaloid (+)-ent-debromoflustramine B

Article abstract of DOI:10.1021/jo00098a011

A diastereoselective synthesis of the unnatural (±)-enantiomer of the marine alkaloid (-)-debromoflustramine B (1) from a cyclic tautomer (9) of L-tryptophan is described. The optical rotation of the synthetic 1 is opposite to that of the natural material