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Concise synthesis of optically active ring-A substituted tryptophans

✍ Scribed by Chunrong Ma; Xiaoxiang Liu; Shu Yu; Shuo Zhao; James M. Cook

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
221 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

A concise synthesis of optically active tryptophan derivatives was developed via diastereoselective alkylation of the Schbllkopf chiral auxiliary 4 to provide alkyne 2 which underwent palladium-catalyzed heteroannulation with iodoanilines 1 to furnish protected tryptophans 3. Hydrolysis and subsequent saponification of 3 provided the desired tryptophans 12 in good yields.

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