Total Synthesis of Sarpagine-Related Bioactive Indole Alkaloids. Chemistry 2018 Feb 16;24(10):2354-2359
Date
12/16/2017Pubmed ID
29244896DOI
10.1002/chem.201705575Scopus ID
2-s2.0-85040792303 (requires institutional sign-in at Scopus site) 25 CitationsAbstract
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 JMAuthor
James M. Cook PhD University Distinguished Professor in the Chemistry and Biochemistry department at University of Wisconsin - MilwaukeeMESH terms used to index this publication - Major topics in bold
AjmalineIndole Alkaloids
Magnetic Resonance Spectroscopy
Molecular Structure
Stereoisomerism
Tryptophan