Two remarkable epimerizations imperative for the success of an asymmetric total synthesis of (+)-aigialospirol

Science China Chemistry

Volumn 54, Issue 1, 2011, Pages 31-42

  Figueroa, Ruth ^a   Feltenberger, John B ^a   Guevarra, Christle C ^a   Hsung, Richard P ^a,b  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b TIANJIN UNIVERSITY   (China)

Author keywords

(+) aigialospirol; and epimerization; anomeric effect; cyclic acetal; tethered RCM

Indexed keywords

(+)-AIGIALOSPIROL; ANOMERIC EFFECT; CYCLIC ACETALS; EPIMERIZATION; TETHERED RCM;

CLIMATE MODELS;

EID: 79251579307     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-010-4176-8     Document Type: Conference Paper

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74. One of the referees kindly pointed out a third approach that could account for either the observed epimerization through the direct formation of the proposed imidanium ion pairs. This insightful suggestion is also plausible and cannot be ruled out especially under the acidic conditions. While it places less significance on the hemi-orthoaminal formation, it accentuates the importance of the amido-group and implies that such epimerization may not take place in the absence of the amido-group