Total synthesis of valeriananoids A, B, and C via autocatalytic diastereoselective domino Michael reaction

被引：15
|
作者：
Fukushima, Masakazu [1 ]
Morii, Akihiro [1 ]
Hoshi, Takashi [2 ]
Suzuki, Toshio [2 ]
Hagiwara, Hisahiro [1 ]
机构：
[1] Niigata Univ, Grad Sch Sci & Technol, Niigata 9502181, Japan
[2] Niigata Univ, Fac Engn, Niigata 9502181, Japan
来源：
TETRAHEDRON | 2007年 / 63卷 / 30期
关键词：
bicyclic aliphatic compounds; tricyclic aliphatic compounds; domino Michael reactions; sesquiterpenoid; valeriananoid;
D O I：
10.1016/j.tet.2007.04.095
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Natural enantiomers of unique tricyclic sesquiterpenoids, valeriananoids A-C 1-3, have been synthesized starting from bicyclo[2.2.2]octane-2,5-dione derivative 11, which was obtained by diastereoselective catalytic domino Michael reaction of oxophorone 5 with 8-phenylmenthyl acrylate 10 by LDA or silica-gel-base (NMAP-Li). The tricyclic ring was closed selectively by intramolecular 6-endo-trig mode cyclization of the ketyl radical, which was generated from keto-allylether 25 by either lithium or sodium naphthalenide. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7154 / 7164
页数：11
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