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A Concise Synthesis of Presilphiperfolane Core through a Tandem TMTU–Co‐Catalyzed Pauson–Khand Reaction and a 6π Electrocyclization Reaction (TMTU=Tetramethyl Thiourea)
Author(s) -
Zhang Zichun,
Li Yuanhe,
Zhao Dandan,
He Yingdong,
Gong Jianxian,
Yang Zhen
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201605438
Subject(s) - thiourea , chemistry , tandem , catalysis , cascade reaction , pauson–khand reaction , carbonylation , reaction conditions , combinatorial chemistry , medicinal chemistry , organic chemistry , stereochemistry , carbon monoxide , materials science , composite material
The synthesis of strained polycyclic systems from readily available precursors with a minimum number of steps and with regio‐ and stereochemical control constitutes an important synthetic challenge. Herein, we report a tandem reaction comprising Co–TMTU (tetramethyl thiourea)‐catalyzed Pauson–Khand (PK) and 6π‐electrocyclization reactions for the formation of the highly strained core of presilphiperfolanols. The developed chemistry has been applied to the total syntheses of 4‐ epi ‐presilphiperfolan‐8‐ol and 7‐ epi ‐presilphiperfolan‐1‐ol.