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Efficient One‐Pot Synthesis of Tetrahydronaphtho[2,1‐ f ]isoquinolines by Using Domino Pictet–Spengler/Friedel–Crafts‐Type Reactions
Author(s) -
Khunnawutmanotham Nisachon,
Sahakitpichan Poolsak,
Chimnoi Nitirat,
Techasakul Supanna
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701243
Subject(s) - isoquinoline , friedel–crafts reaction , chemistry , domino , aldehyde , pictet–spengler reaction , substrate (aquarium) , alkaloid , one pot synthesis , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , oceanography , geology
This study describes a facile and efficient one‐pot method for the synthesis of a tetrahydronaphtho[2,1‐ f ]isoquinoline alkaloid. An N ‐protected amino aldehyde biaryl substrate underwent domino Pictet–Spengler/Friedel–Crafts‐type cyclization reactions to produce the tetrahydronaphtho[2,1‐ f ]isoquinoline skeleton. Litebamine, a naturally occurring compound, was prepared by using the proposed approach to exemplify its utility.