Efficient One‐Pot Synthesis of Tetrahydronaphtho[2, 1‐f]isoquinolines by Using Domino Pictet–Spengler/Friedel–Crafts‐Type Reactions. Issue 43 (22nd November 2017)

• Record Type: Journal Article
• Authors: Khunnawutmanotham, Nisachon; Sahakitpichan, Poolsak; Chimnoi, Nitirat; Techasakul, Supanna
• Is Part Of: European journal of organic chemistry. Issue 43(2017)
• Page Start: 6434
• Page End: 6440
• Publication Date: 2017-11-22
• Subjects: Synthetic methods -- Nitrogen heterocycles -- Cyclization -- Domino reactions -- Alkaloids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701243
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : A facile and efficient one‐pot method for the synthesis of a tetrahydronaphtho[2, 1‐ f ]isoquinoline alkaloid by using domino Pictet–Spengler/Friedel–Crafts‐type cyclization reactions has been reported. Litebamine, a naturally occurring compound, was prepared by using this proposed approach to exemplify its utility.