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7749577 
Journal Article 
Intramolecular imino Diels-Alder reaction of a 3-vinyl indole: Application to a total synthesis of (+/-)-eburnamonine 
Grieco, PA; Kaufman, MD 
1999 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
AMER CHEMICAL SOC 
WASHINGTON 
64 
20 
7586-7593 
English 
WOS:000083036800042 
The intramolecular [4 + 2] cycloaddition of imine 1 has been examined under a variety of conditions including thermal; catalysis by acid, lithium cation, and Florisil; and the use of 5.0 M lithium perchlorate in diethyl ether. Cycloadduct 2 was transformed into (±)-eburnamonine 3 using acid catalysis. Substrate 1 was prepared by coupling indole-3-carboxaldehyde 7 with the activated p-mitrophenyl ester 9. Subsequent methylenation of 10 gave rise to 11, which upon exposure to fluoride ion provided imine 1.