NMR assignments and absolute stereochemistry of two guaianolide sesquiterpenes from  Tanacetum densume  subsp. amani | Zendy

Ulubelen Ayhan | Zendy; Gören Nezhun | Zendy; Jiang TianYi | Zendy; Scott Lincoln | Zendy; TianasoaRamomojy Manoelson | Zendy; Snyder John M. K. | Zendy

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NMR assignments and absolute stereochemistry of two guaianolide sesquiterpenes from Tanacetum densume subsp. amani

Author(s) -

Ulubelen Ayhan,

Gören Nezhun,

Jiang TianYi,

Scott Lincoln,

TianasoaRamomojy Manoelson,

Snyder John M. K.

Publication year - 1995

Publication title -

magnetic resonance in chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.483

H-Index - 72

eISSN - 1097-458X

pISSN - 0749-1581

DOI - 10.1002/mrc.1260331111

Subject(s) - chemistry , sesquiterpene , asteraceae , stereochemistry , absolute (philosophy) , absolute configuration , ketone , germacranolide , sesquiterpene lactone , botany , organic chemistry , biology , philosophy , epistemology

The guaianolide sesquiterpene pyrethroidinin (1) and the corresponding ketone parishin A (2) wee isolated from Tanacetum densum subsp. amani (Asteraceae). The absolute stereochemistry of 1 was established as (1 R , 3 R , 6 S , 7 S , 10 R ) on the basis of the differential shielfing in the 1 H NMR spectra of the (−)‐ and (+)‐ O ‐methylmandelate esters. The structure, including absolute stereochemistry, of 2 was confirmed by oxidation of 1 whit Jones' reagent.

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