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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).