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Synthese der vier stereoisomeren Dihydropalustraminsäuren. 13. Mitteilung über Schachtelhalmalkaloide
Author(s) -
Wálchli Peter Christian,
Eugster Conrad Hans
Publication year - 1978
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.19780610236
Subject(s) - chemistry , piperidine , stereospecificity , ring (chemistry) , diastereomer , stereochemistry , benzylamine , reagent , acetic acid , organic chemistry , catalysis
Syntheses of the four stereoisomeric dihydropalustramic acids ([6‐(1‐hydroxypropyl)‐2‐piperidyl]acetic acids) (−)‐Dihydropalustramic acid, a key product in the structure elucidation of the alkaloid palustrin, has been assigned the threo‐cis structure 20 by comparison with the four stereoisomeric (±)‐dihydropalustramic acids (threo‐cis, threo‐trans, erythro‐cis, erythro‐trans). The latter were synthesized by a new route to α, α′‐di‐substituted piperidines of this type. Ring closure to the piperidine ring with simultaneous stereospecific formation of the hydroxylated side chain has been achieved by reaction of the stereoisomeric methylesters of 7,8‐epoxy‐2‐decenoic acids with benzylamine. Assignment of the configuration at the piperidine ring is based on careful comparison of the H‐NMR. spectra of the N‐benzylpiperidines and with the help of lanthanide shift reagents.