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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 11
BKCSDE 31(11)
November 20, 2010 

Total Synthesis of (±)-Aspidospermidine Starting from 3-Ethyl-5-bromo-2-pyrone
Hyun Kyu Cho, Nguyen Thanh Tam, Cheon Gyu Cho*
Total synthesis, Aspidospermidine, Diels-Alder reaction, 3,5-Dibromo-2-pyrone, Tandem reaction
A new synthetic route to (±)-aspidospermidine was devised, starting from the cycloadduct of 3-ethyl-5-bromo-2- pyrone with vinyl sulfide through a tandem conjugate addition-alkylation sequence. The requisite 3-ethyl-5-bromo-2- pyrone was prepared via the C3-selective Pd-catalyzed coupling reaction with Et3Al-dimethylaminoethanol complex.
3382 - 3384
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