Synthese des Pyrrolizidin‐Alkaloides (±)‐Trachelanthamidin | Zendy

Horni Albert | Zendy; Hubáček Ivana | Zendy; Hesse Manfred | Zendy

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Synthese des Pyrrolizidin‐Alkaloides (±)‐Trachelanthamidin

Author(s) -

Horni Albert,

Hubáček Ivana,

Hesse Manfred

Publication year - 1994

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19940770221

Subject(s) - chemistry , pyrrolizidine , nitromethane , pyrrolidine , alkaloid , diastereomer , pyrrolizidine alkaloid , derivative (finance) , stereochemistry , alcohol , hydrochloride , isoquinoline , organic chemistry , financial economics , economics

Synthesis of the Pyrrolizidine Alkaloid (±)‐Trachelanthamidine The important intermediate in the synthesis of the title compound 8 is the diastereoisomer mixture of ethyl 2‐[2‐(1,3 dioxolan‐2‐yl)ethyl]‐5‐oxopyrrolidine‐3‐carboxylate ( 3a/3b ) which was prepared from nitromethane, acrylaldehyde, and diethyl fumarate ( Scheme ). Its reduction (NaBH 4 , t ‐BuOH, MeOH) gave exclusively the trans ‐alcohol 4a , which was converted to the protected pyrrolidine derivative 6 . The deprotection and reduction of 6 gave the pyrrolizidine alkaloid 8 , characterized as its hydrochloride.

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