Chirality · 1997 · 16 citations · 15 references
PharmacyChemistryMedicinal ChemistryNatural Product BiosynthesisOrganic ChemistrySynthetic Medicinal ChemistryAlkaloid BiosynthesisHeterocyclic ChemistryMacrocycle SynthesisAbsolute Configuration AssignmentAbsolute Configuration DeterminationBiosynthetic Intermediates In Alkaloid PathwaysChiralityChirality DeterminationConfiguration At Chiral CentersLactam MacrocyclesLactam Synthesis
In this short review of several macrocyclic spermidine alkaloids, special consideration has been given to the correct determination of the absolute configuration at their chiral centers. The bases of interest are characterized by possessing a 13-membered macrocyclic lactam ring incorporating spermidine and either cinnammic or fatty acid precursorial units. In this context, the synthesis of some of these alkaloids is presented and the first total synthesis of optically pure (+)-(S)-viburnine, and (−)-(S)-celafurine is reported. Finally, a common initial step in biosynthesis starting with an enzyme-catalyzed Michael addition of spermidine to an α,β-unsaturated acid is proposed. Chirality 9:523–528, 1997. © 1997 Wiley-Liss, Inc.
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Cannabisativine, a new alkaloid from cannabis sativa l. root
Hermann L. Latter, Donald J. Abraham, Carlton E. Turner et al. · Tetrahedron Letters · 1975 · 48 citations