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Asymmetric Total Synthesis of Hispidanin A
Author(s) -
Deng Heping,
Cao Wei,
Liu Rong,
Zhang Yanhui,
Liu Bo
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201700958
Subject(s) - stille reaction , chemistry , labdane , polyene , alkene , cycloaddition , cationic polymerization , total synthesis , catalysis , diene , stereochemistry , combinatorial chemistry , organic chemistry , terpenoid , natural rubber
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.