First total syntheses of the 1,2,3,4-tetrahydronaphtho[2,1- f]isoquinolines annoretine and litebamine

We describe here the first total synthesis of the two natural 1,2,3,4-tetrahydronaphtho[2,1- f]isoquinolines, annoretine and litebamine, from [2-(2-styrylphenyl)ethyl]methylcarbamic acid ethyl esters. The key steps were the Bischler–Napieralski cyclization to form the isoquinoline unit and photocycl...

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Bibliographic Details
Published in:Tetrahedron 2003-09, Vol.59 (40), p.8057-8065
Main Authors: Pampı́n, M.Carme, Estévez, Juan C, Estévez, Ramón J, Suau, Rafael, Castedo, Luis
Format: Article
Language:English
Subjects:
Bischler–Napieralski cyclization
demethylation
Heck reaction
isoquinoline
photocyclization
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Summary:We describe here the first total synthesis of the two natural 1,2,3,4-tetrahydronaphtho[2,1- f]isoquinolines, annoretine and litebamine, from [2-(2-styrylphenyl)ethyl]methylcarbamic acid ethyl esters. The key steps were the Bischler–Napieralski cyclization to form the isoquinoline unit and photocyclization of the resulting 2-methyl-5-styryl-3,4-dihydro-2 H-isoquinolin-1-ones to 2-methyl-3,4-dihydro-2 H-naphtho[2,1- f]isoquinolin-1-ones. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(03)01135-9