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Synthesis of Azapolycyclic Systems via the Intramolecular [4 + 2] Cycloaddition Chemistry of 2-(Alkylthio)-5-amidofurans.

✍ Scribed by Albert Padwa; John D. Ginn; Scott K. Bur; Cheryl K. Eidell; Stephen M. Lynch


Publisher
John Wiley and Sons
Year
2010
Weight
39 KB
Volume
33
Category
Article
ISSN
0931-7597

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✦ Synopsis


Abstract

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Efficient Asymmetric Synthesis of Pumili
✍ Wolfgang Oppolzer; Elmar Flaskamp; Lotharβ€…W. Bieber πŸ“‚ Article πŸ“… 2001 πŸ› John Wiley and Sons 🌐 German βš– 72 KB πŸ‘ 2 views

An efficient asymmetric synthesis in nine steps of natural (Γ€)-pumiliotoxin C (1), a decahydroquinoline alkaloid found in the skin of Central American frog species, is presented. The enantiomerically pure starting material (S)-norvalinol (3), obtained from commercial (S)-norvaline, was cyclized in a