Stereoselective synthesis and structural correction of the naturally occurring lactone stagonolide G

Organic Letters

Volumn 12, Issue 24, 2010, Pages 5752-5755

  Angulo Pachón, César A ^a   Díaz Oltra, Santiago ^a   Murga, Juan ^a   Carda, Miguel ^a   Marco, J Alberto ^b  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE; SINGLE HETEROCYCLIC RINGS; STAGONOLIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; HETEROCYCLIC COMPOUNDS, 1-RING; LACTONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 78650363381     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102599e     Document Type: Article

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50. For natural lactones containing additional free hydroxyl groups, the question remains open as to whether they all are true natural products or some of them are the result of translactonization process during the isolation. In the present case, it is not unlikely that the natural product actually has structure 1, which then isomerized during the isolation to the more stable -lactone 16.
51. 3 (taken from a bottle opened a few weeks prior to use) already showed incipient NMR signals of 16 after several minutes at room temperature. After 15 h, about 50% of 1 was converted into 16. Interestingly, lactone 15 did not show this marked proclivity to acid-catalyzed translactonization.
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