Total synthesis of (+)-kopsihainanine A

Total synthesis of (+)-kopsihainanine A was accomplished on the basis of (i) Stoltz's enantioselective decarboxylative asymmetric allylation and (ii) the proposed biogenetic pathway from the related alkaloid, kopsihainanine B. In addition, HPLC analysis of the synthetic (+)-kopsihainanine A con...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 50; no. 43; pp. 5782 - 5785
Main Authors Mizutani, Masaya, Yasuda, Shigeo, Mukai, Chisato
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.06.2014
Subjects
Alkaloids
Allyl compounds
Asymmetry
Chemical reactions
Chemistry
Chemistry Techniques, Synthetic
Chemistry, Multidisciplinary
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Pathways
Physical Sciences
Science & Technology
Stereoisomerism
Substrate Specificity
Synthesis
SYSTEM
DIHYDROXYLATION
CARBAZOLONES
CATALYZED DECARBOXYLATIVE ALLYLATION
ALKALOIDS
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Summary:Total synthesis of (+)-kopsihainanine A was accomplished on the basis of (i) Stoltz's enantioselective decarboxylative asymmetric allylation and (ii) the proposed biogenetic pathway from the related alkaloid, kopsihainanine B. In addition, HPLC analysis of the synthetic (+)-kopsihainanine A confirmed its ee to be 99% with [alpha](D)(30) = 25.35.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc01843e