Organic Process Research and Development p. 442 - 446 (2008)
Update date:2022-08-11
Topics:
Oda, Katsuo
Hida, Takemasa
Sakata, Terao
Nagai, Masahiko
Sugata, Yoshihide
Masui, Toshiaki
Nogusa, Hideo
A one-pot synthesis of S-2474 was developed to overcome the problems of a large number of steps, low stereoselectivity, low yield, a large amount of waste, and severe reaction conditions. Aldol-type condensation of 3,5-di-terf-butyl-4-hydroxybenzaldehyde and iV-ethyl-γsultam was carried out with LDA and then quenched with water. Dehydration proceeded under basic conditions, providing S-2474 directly as a single isomer on the benzylidene double bond. The reaction mechanism appears to involve a quinone methide intermediate. Environmental assessment of the development of this compound is also discussed in this paper.
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