Total Synthesis of Taiwaniadducts B, C, and D

The first total syntheses of taiwaniadducts B, C, and D have been accomplished. Two diterpenoid segments were prepared with high enantiopurity, both through Ir-catalyzed asymmetric polyene cyclization. A sterically demanding intermolecular Diels–Alder reaction promoted by Er­(fod)3 assembled the sca...

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Published inJournal of the American Chemical Society Vol. 136; no. 23; pp. 8185 - 8188
Main Authors Deng, Jun, Zhou, Shupeng, Zhang, Wenhao, Li, Jian, Li, Ruofan, Li, Ang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 11.06.2014
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclization
Cycloaddition Reaction
Diterpenes - chemical synthesis
Diterpenes - chemistry
Models, Molecular
Molecular Structure
Physical Sciences
Science & Technology
DITERPENES
DIELS-ALDER REACTIONS
IRIDIUM
TAIWANIAQUINOIDS
QUINONES
CYCLOADDUCTS
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Summary:The first total syntheses of taiwaniadducts B, C, and D have been accomplished. Two diterpenoid segments were prepared with high enantiopurity, both through Ir-catalyzed asymmetric polyene cyclization. A sterically demanding intermolecular Diels–Alder reaction promoted by Er­(fod)3 assembled the scaffold of taiwaniadducts B and C. A carbonyl-ene cyclization forged the cage motif of taiwaniadduct D at a late stage, providing over 200 mg of this compound.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja503972p