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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 28, Number 8
BKCSDE 28(8)
August 20, 2007 

Synthesis of Calycotomine via Pictet-Spengler Type Reaction of N,O-Acetal TMS Ethers as N-Acyliminium Ion Equivalents
Jung-Eun Yang, Jin-Kyung In, Mi-Sung Lee, Jae-Hwan Kwak, Heesoon Lee, Soo Jae Lee, Han-Young Kang, Young-Ger Suh*, Jae-Kyung Jung*
Tetrahydroisoquinoline, Pictet-Spengler reaction, N,O-Acetal TMS ether, Alkaloid
An efficient Pictet-Spengler type reaction of N,O-acetal TMS ethers for the practical synthesis of 1-substituted tetrahydroquinolines, medicinally important alkaloids, has been accomplished. To demonstrate the versatility of this novel procedure, the total synthesis of calycotomine, a representative 1-hydroxymethyl substituted tetrahydroisoquinoline, is also described.
1401 - 1404
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