Asymmetric Total Synthesis of Hispidanin A

Asymmetric total synthesis of the dimeric diterpenoid hispidanin A was accomplished by non‐catalytic Diels–Alder cycloaddition at room temperature. The synthesis relies on iron‐catalyzed coupling to construct a Z‐configured trisubstituted alkene, an iron‐catalyzed radical cascade to generate a labda...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 56; no. 21; pp. 5849 - 5852
Main Authors Deng, Heping, Cao, Wei, Liu, Rong, Zhang, Yanhui, Liu, Bo
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 15.05.2017
Subjects
Chemistry
Chemistry, Multidisciplinary
diterpenoids
labdane
Physical Sciences
radical cascade
Science & Technology
total synthesis
totarane
ACID
COMPLEXES
radical cascade
YUENNANENSIS
OXIDATION-REDUCTION HYDRATION
diterpenoids
totarane
DIELS-ALDER REACTION
CONDENSATION
labdane
total synthesis
OLEFIN
CYCLIZATION
RHIZOMES
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Summary:Asymmetric total synthesis of the dimeric diterpenoid hispidanin A was accomplished by non‐catalytic Diels–Alder cycloaddition at room temperature. The synthesis relies on iron‐catalyzed coupling to construct a Z‐configured trisubstituted alkene, an iron‐catalyzed radical cascade to generate a labdane‐type diene, and both Yamamoto cationic polyene cyclization and palladium‐catalyzed Stille coupling to generate a totarane‐type dienophile. Radical is radical: Asymmetric total synthesis of a dimeric diterpenoid, hispidanin A, has been accomplished through spontaneous [4+2] cycloaddition without catalysis at room temperature. Construction of the diene fragment features a designed radical polyene cyclization triggered by metal‐catalyzed hydrogen atom transfer, while subsequent asymmetric cationic polyene cyclization generates the dienophile fragment.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201700958