1H- und 13C-NMR.-spektroskopische Untersuchungen an den vier diastereomeren (±)-Dihydropalustraminsäure-methylestern; Strukturkorrelation mit (−)-Dihydropalustraminsäure-methylester sowie mit dem Alkaloid Palustrin. 14. Mitteilung über Schachtelhalmalkaloide
✍ Scribed by Peter Rüedi; Conrad Hans Eugster
- Publisher
- John Wiley and Sons
- Year
- 1978
- Tongue
- German
- Weight
- 362 KB
- Volume
- 61
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
^1^H‐and^13^C‐NMR. spectra of methyl esters of the diastereomeric (±)‐dihydropalustramic acids; structural correlation of (−)‐dihydropalustramic acid with the alkaloid palustrin
Unambiguous assignment of cis‐trans configuration at the piperidine ring of the four diastereomeric methyl esters of the (±)‐dihydropalustramic acids is based on the interpretation of ^1^H‐ and ^13^C‐NMR. data. (−)‐Dihydropalustramic acid, the important degradation product of the alkaloid palustrin is shown to be threo‐cis‐[6‐(1‐hydroxypropyl)‐2‐piperidyl]acetic acid. The same conclusion holds for palustrin and dihydropalustrin. Therefore, palustrin is threo‐cis‐17‐(1‐hydroxy‐propyl)‐1,5,10‐triazabicyclo[11.4.0]heptadec‐15‐en‐11‐one.