Enantioselective Total Synthesis of (−)-Erinacine B

The first enantioselective total synthesis of (−)-erinacine B has been achieved. Our approach features convergent construction of the 5-6-7 tricyclic cyathane core system via chiral building blocks prepared using asymmetric catalysis developed by us and highly stereoselective construction of all ste...

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Bibliographic Details
Published inOrganic letters Vol. 9; no. 2; pp. 359 - 362
Main Authors Watanabe, Hideaki, Takano, Masashi, Umino, Akinori, Ito, Toshiya, Ishikawa, Hiroyuki, Nakada, Masahisa
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.01.2007
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Diterpenes - chemistry
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Ketones - chemistry
Molecular Conformation
Physical Sciences
Saccharomyces cerevisiae - chemistry
Science & Technology
Stereoisomerism
ASYMMETRIC CATALYSIS
CYATHIN DITERPENES
(+)-ERINACINE
HERICIUM-ERINACEUM
(+)-ALLOCYATHIN B-2
ERINACINES
MYCELIA
(+/-)-ALLOCYATHIN B-2
METABOLITE
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Summary:The first enantioselective total synthesis of (−)-erinacine B has been achieved. Our approach features convergent construction of the 5-6-7 tricyclic cyathane core system via chiral building blocks prepared using asymmetric catalysis developed by us and highly stereoselective construction of all stereogenic centers in the aglycon.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0628816