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Total Synthesis of Sarpagine-Related Bioactive Indole Alkaloids. Chemistry 2018 Feb 16;24(10):2354-2359

Date

12/16/2017

Pubmed ID

29244896

DOI

10.1002/chem.201705575

Scopus ID

2-s2.0-85040792303 (requires institutional sign-in at Scopus site)   25 Citations

Abstract

Extension of the asymmetric Pictet-Spengler reaction to bulkier Nb -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.

Author List

Rahman MT, Deschamps JR, Imler GH, Cook JM

Author

James M. Cook PhD University Distinguished Professor in the Chemistry and Biochemistry department at University of Wisconsin - Milwaukee




MESH terms used to index this publication - Major topics in bold

Ajmaline
Indole Alkaloids
Magnetic Resonance Spectroscopy
Molecular Structure
Stereoisomerism
Tryptophan