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Influence of conformational factors on acid‐catalyzed cyclizations of germacranolides: Molecular structure of the cyclization products of gallicin and 8α‐hydroxygallicin (shonachalin a)
Author(s) -
Marco J. Alberto,
SanzCervera Juan F.,
GarcíaLliso Vicente,
Domingo Luis R.,
Carda Miguel,
Rodríguez Santiago,
LópezOrtiz Fernando,
Lex Johann
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199510257
Subject(s) - chemistry , germacranolide , stereochemistry , catalysis , organic chemistry , lactone
Acid‐catalyzed cyclization of the natural germacranolide gallicin ( 8 ) yielded, among other products, the 1,4‐epoxyeudes‐manolide 9 , which has a trans ‐fused decaline system. Under the same conditions the closely related germacranolide shonachalin A (8α‐hydroxygallicin) ( 3 ) cyclized to the eudesmanolide 4 with a cis fused decaline system. The structures of these cyclization products were secured by means of chemical correlations and X‐ray diffraction analyses.