4 years ago

Asymmetric Total Synthesis of Hispidanin A

Asymmetric Total Synthesis of Hispidanin A
Heping Deng, Rong Liu, Bo Liu, Wei Cao, Yanhui Zhang
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.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700958

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