Alpha-amination of labdane-type diterpenes by organocatalysis

The first electrophilic α-amination reaction of labdane-type diterpene (−)-(5S,9S,10S,13S)-labd-7-en-15-oic acid and (+)-(5S,8R,9R,10S,13R)-8-hydroxylabdan-15-oic acid, isolated from aerial parts of Ageratina jocotepecana is presented. In the presence of dibenzylazodicarboxylate and proline followed...

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Bibliographic Details
Published inSynthetic communications Vol. 52; no. 3; pp. 451 - 461
Main Authors Calderón-Rangel, David, García-Gutiérrez, Hugo A., del Río, Rosa E., Thomassigny, Christine
Format Journal Article
LanguageEnglish
Published Philadelphia Taylor & Francis 01.02.2022
Taylor & Francis Ltd
Taylor & Francis: STM, Behavioural Science and Public Health Titles
Subjects
13-epi-labdanolic acid
Ageratina jocotepecana
Alcohols
amination
cativic acid
Chemical Sciences
diasteromers
organocatalysis
Stereoselectivity
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Summary:The first electrophilic α-amination reaction of labdane-type diterpene (−)-(5S,9S,10S,13S)-labd-7-en-15-oic acid and (+)-(5S,8R,9R,10S,13R)-8-hydroxylabdan-15-oic acid, isolated from aerial parts of Ageratina jocotepecana is presented. In the presence of dibenzylazodicarboxylate and proline followed by an in situ reduction, the corresponding hydrazino alcohols were obtained. It is demonstrated that the first diterpene moiety had no influence in the diastereoselectivity that is then controlled by the catalyst used, at the opposite to the second diterpene that mainly control the diastereochemistry of the product.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2022.2032174