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Stereoselective Construction of Cisoidal Bisspiroacetal Frameworks through Magnesium Coordination of the Bilateral Acetal Oxygen Atoms
Author(s) -
Yasukawa Yoshifumi,
Tsuchikawa Hiroshi,
Todokoro Yasuto,
Murata Michio
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800074
Subject(s) - chemistry , acetal , stereoselectivity , magnesium , oxygen atom , chelation , ring (chemistry) , oxygen , stereochemistry , catalysis , organic chemistry , molecule
The cisoid ‐selective construction of a tricyclic bisspiroacetal framework was demonstrated using MgBr 2 as a cisoid stabilizer through chelation of the oxygen atoms of lateral acetal rings in the cisoid configuration. The method was also successfully applied to substrates with different ring sizes and substituents. Thus, this method serves as a useful synthetic strategy for the total synthesis of bisspiroacetal‐containing natural products.