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Use of an acetylenic sulfone as an alkene dipole equivalent in the synthesis of (±)-pumiliotoxin C

✍ Scribed by Thomas G. Back; Katsumasa Nakajima

Book ID
104256251
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
217 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The cycloaddition of methyl c/s-2-amino-trans-6-methyleyclohexaneearboxylate (.,1) with 1-p-(toluenesulfonyl)-l-pentyne (4) afforded the corresponding enaminone 2, that was in turn reduced to (:l:)-pumiliotoxin C (1). The acetylenic sulfone 4 thus functions as the synthetic ecluivalent of the alkene dipole 5 in this process.

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ChemInform Abstract: Enantioselective Sy
ChemInform Abstract: Enantioselective Synthesis of (-)-Pumiliotoxin C from a Chiral Amino Ester and an Acetylenic Sulfone that Acts as an Alkene Dipole Equivalent.
✍ T. G. BACK; K. NAKAJIMA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 1 views

Enantioselective Synthesis of (-)-Pumiliotoxin C from a Chiral Amino Ester and an Acetylenic Sulfone that Acts as an Alkene Dipole Equivalent. -A new synthesis of the natural enantiomer of the dendrobatid alkaloid pumiliotoxin C (VII) which acts as reversible blocker of the nicotinic acetylcholine