Synthese von (1α,7α,8β)‐(±)‐7‐Hydroxy‐1‐(hydroxymethyl)pyrrolizidin, der Necin‐Base  rac ‐Platynecin | Zendy

Röder Erhard | Zendy; Bourauel Thomas | Zendy; Wiedenfeld Helmut | Zendy

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Synthese von (1α,7α,8β)‐(±)‐7‐Hydroxy‐1‐(hydroxymethyl)pyrrolizidin, der Necin‐Base rac ‐Platynecin

Author(s) -

Röder Erhard,

Bourauel Thomas,

Wiedenfeld Helmut

Publication year - 1990

Publication title -

liebigs annalen der chemie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0170-2041

DOI - 10.1002/jlac.1990199001113

Subject(s) - chemistry , saponification , hydroxymethyl , alkylation , decarboxylation , pyrrolizidine , stereochemistry , medicinal chemistry , organic chemistry , catalysis

Synthesis of (1α,7α,8β)‐(±)‐7‐Hydroxy‐1‐(hydroxymethyl)pyrrolizidin, the Necine rac ‐Platynecine rac ‐Platynecine ( rac ‐ 7 ) can easily be obtained in high yields from diethyl (±)‐ cis ‐2,3‐pyrrolidinedicarboxylate ( rac ‐ 1 ) by N ‐alkylation to ethyl (±)‐ cis ‐2,3‐bis(ethoxycarbonyl)‐1‐pyrrolidinepropionate ( rac ‐ 2 ), Dieckmann reaction to ethyl (1α,8β)‐(±)‐6‐ethoxycarbonyl‐7‐oxo‐1‐pyrrolizidinecarboxylate ( rac ‐ 3 ), subsequent saponification, decarboxylation, reduction to (1α,7α,8β)‐(±)‐pyrrolizidine‐1,7‐carbolactone ( rac ‐ 6 ), and further reduction to the desired title compound rac ‐ 7 .

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