Gold(I)‐Catalyzed Bis‐Spiroketalization: Synthesis of the Trioxadispiroketal‐Containing A–D Rings of Azaspiracid | Zendy

Li Yongfeng | Zendy; Zhou Feng | Zendy; Forsyth Craig J. | Zendy

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Gold(I)‐Catalyzed Bis‐Spiroketalization: Synthesis of the Trioxadispiroketal‐Containing A–D Rings of Azaspiracid

Author(s) -

Li Yongfeng,

Zhou Feng,

Forsyth Craig J.

Publication year - 2006

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200601963

Subject(s) - tetrahydrofuran , ring (chemistry) , alkyne , catalysis , chemistry , combinatorial chemistry , bridging (networking) , stereochemistry , organic chemistry , computer science , solvent , computer network

Au‐dacious ring synthesis : An efficient synthesis of the A–D rings of azaspiracid has been developed by using a Co‐catalyzed oxaetherification to form the fused 2,5‐ trans ‐configured trisubstituted tetrahydrofuran D ring, and an unprecedented Au‐catalyzed bis‐spiroketal formation wherein a bridging alkyne served as a surrogate for the C10 ketal (see scheme; PMB= para ‐methoxybenzyl, TBDPS= tert ‐butyldiphenylsilyl).

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