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Concise synthesis of the cell cycle inhibitor demethoxyfumitremorgin C

✍ Scribed by Haishan Wang; Arasu Ganesan

Book ID
104257252
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
119 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Reaction of the imine derived from L-tryptophan methyl ester and senecialdehyde with Fmoe-L-Pro-Cl induces an acyliminium Pictet-Spengler condensation, yielding a mixture of cis and trans tetrahydro-13-carbolines. Deprotection of the cis product with concomitant diketopiperazine formation afforded the natural product in 20 % overall yield.

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