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The aza-xylylene Diels–Alder approach for the synthesis of naturally occurring 2-alkyl tetrahydroquinolines

✍ Scribed by Frank Avemaria; Sylvia Vanderheiden; Stefan Bräse

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
297 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

The recently discovered intramolecular aza-xylylene Diels -Alder reaction, based on a 1,4-dehydrohalogenation reaction, was extended in terms of substrates and leaving groups allowing the assembly of tetrahydroquinolines in two synthetic steps. Intramolecular cleavage of a thiocarbamate using triphenylphosphine and tetrachloromethane (Appel conditions) to give chloromethyl phenylisocyanate has been presented for the first time. The synthetic feasibility of this process was demonstrated in the first total syntheses of the alkaloids rac-Angustureine and 1-methyl-2-propyltetrahydroquinoline.

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