TANDEM [4+2] [3+2] CYCLOADDITIONS OF NITROALKENES .13. THE SYNTHESIS OF (-)-DETOXININE/

Authors
DENMARK SE HURD AR SACHA HJ
Citation
Se. Denmark et al., TANDEM [4+2] [3+2] CYCLOADDITIONS OF NITROALKENES .13. THE SYNTHESIS OF (-)-DETOXININE/, Journal of organic chemistry, 62(6), 1997, pp. 1668-1674
Citations number
71
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
6
Year of publication
1997
Pages
1668 - 1674
Database
ISI
SICI code
0022-3263(1997)62:6<1668:T[[CON>2.0.ZU;2-L
Abstract
(-)-Detoxinine, an unusual, highly-functionalized amino acid, is the c ore residue of many components that comprise the detoxin complex. The synthesis of(-)-detoxinine was accomplished in 10 steps and 13.4% over all yield from commercially available dichlorodiisopropylsilane. The k ey step is an asymmetric tandem inter [4 + 2]/intra [3 + 2] cycloaddit ion between silyoxynitroalkene 17 and chiral vinyl ether (-)-24, illus trating the application of a temporary silicon tether in the tandem ni troalkene cycloaddition process.