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A diels-alder approach to functionalised cis-hydroisoquinolines

✍ Scribed by Dennis de Oliveira Imbroisi; Nigel S. Simpkins

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
243 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new substituted 5,6-dihydro-2(lH)-pyridinone participates in highly efficient Diels-Alder reactions to give functional&d cis-hydroisoquinolines suitable for natural product synthesis.

The cis-hydroisoquinoline ring system constitutes an important part of natural products such as the indole alkaloid reserpine (1). Ii addition, both cis and rrans isomers have importance as synthetic intermediates in the synthesis of morphine alkaloids (e.g. morphine ( 2)), and their analogues, which are of considerable pharmacological interest. Most recently the isolation of the potent antileukemic alkaloid manzamine A (3) served to further focus our interest on the synthesis of highly substituted and functionalised cis-hydroisoquinolines.1

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