1. Total Synthesis of Sarpagine-Related Bioactive Indole Alkaloids.
- Author
-
Rahman MT, Deschamps JR, Imler GH, and Cook JM
- Subjects
- Ajmaline chemical synthesis, Magnetic Resonance Spectroscopy methods, Molecular Structure, Oxindoles, Stereoisomerism, Indole Alkaloids chemical synthesis, Tryptophan analogs & derivatives, Tryptophan chemical synthesis
- Abstract
Extension of the asymmetric Pictet-Spengler reaction to bulkier N
b -alkylated tryptophan derivatives resulted in an improved stereospecific access to the key bicyclo[3.3.1]nonane core of bioactive C-19 methyl substituted sarpagine/macroline/ajmaline indole alkaloids with excellent diastereoselectivity by internal asymmetric induction. Complete stereocontrol of the C-19 methyl function in either the α- or β-configuration was achieved, which enables the total synthesis of any member from this group of thirty alkaloids. We report herein, the total synthesis of macrocarpines (A-C) 1-3, talcarpine 4, N(4)-methyl-N(4),21-secotalpinine 5, dihydroperaksine 8 and deoxyperaksine 9., (© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)- Published
- 2018
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