Total Synthesis of (+)‐Rutamarin

The first enantioselective total synthesis of (+)‐rutamarin (1) is described. The synthetic route features the highly enantioselective construction of the stereogenic center via the Sharpless asymmetric dihydroxylation (99% ee), the facile assembly of quaternary carbon‐centered 3‐substituted side ch...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 350; no. 14‐15; pp. 2373 - 2379
Main Authors Zhang, Yi‐Nan, Zhang, Shi‐Lei, Ma, Lei, Zhang, Yu, Shen, Xu, Wang, Wei, Hu, Li‐Hong
Format Journal Article
LanguageEnglish
Published Weinheim WILEY‐VCH Verlag 06.10.2008
Wiley
Subjects
asymmetric synthesis
Chemistry
Chemistry, Applied
Chemistry, Organic
furanocoumarins
Physical Sciences
rutamarin
Science & Technology
Sharpless asymmetric dihydroxylation
3-(1',1'-DIMETHYLALLYL)COUMARINS
rutamarin
asymmetric synthesis
furanocoumarins
Sharpless asymmetric dihydroxylation
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Summary:The first enantioselective total synthesis of (+)‐rutamarin (1) is described. The synthetic route features the highly enantioselective construction of the stereogenic center via the Sharpless asymmetric dihydroxylation (99% ee), the facile assembly of quaternary carbon‐centered 3‐substituted side chain and high synthetic efficiency from readily available starting materials. Furthermore, the synthetic strategy could be readily adopted for the synthesis of (+)‐rutamarin analogues.
Bibliography:ObjectType-Article-2
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content type line 23
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200800396