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Front Cover: Direct Access to (±)‐10‐Desbromoarborescidine A from Tryptamine and Pentane‐1,5‐diol (Asian J. Org. Chem. 6/2020)
Author(s) -
Sahoo Apurba Ranjan,
Lalitha Gummidi,
Murugesh V.,
Bruneau Christian,
Sharma Gangavaram V. M.,
Suresh Surisetti,
Achard Mathieu
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000252
Subject(s) - chemistry , tryptamine , pentane , ruthenium , diol , combinatorial chemistry , phosphine , catalysis , formal synthesis , stereochemistry , organic chemistry , biochemistry
An environmentally benign single step synthetic strategy for the indoloquinolizidine alkaloid, (±)‐10‐desbromoarborescidine A has been achieved. This formal dehydrogenative dehydrative coupling of tryptamine and pentane‐1,5‐diol is efficiently catalyzed by a ruthenium catalyst featuring a proton responsive phosphine‐pyridone ligand. This is a remarkable one‐step synthesis of (±)‐10‐desbromoarborescidine A from saturated alkylating agents. This simple, yet powerful protocol has potential utility in repurposing traditional synthetic approaches for various indoloquinolizidine and harmicine alkaloids. More information can be found in the Communication by Mathieu Achard et al.

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