Efficient Enantioselective Syntheses of (+)-Dalesconol A and B | Zendy

Guoqing Zhao | Zendy; Guangqing Xu | Zendy; Chao Qian | Zendy; Wenjun Tang | Zendy

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Efficient Enantioselective Syntheses of (+)-Dalesconol A and B

Author(s) -

Guoqing Zhao,

Guangqing Xu,

Chao Qian,

Wenjun Tang

Publication year - 2017

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.7b00783

Subject(s) - chemistry , enantioselective synthesis , stille reaction , kinetic resolution , combinatorial chemistry , stereochemistry , steric effects , degree of unsaturation , tandem , ring (chemistry) , stereocenter , organic chemistry , catalysis , materials science , composite material

We herein report the first enantioselective syntheses of immunosuppressants (+)-dalesconol A and B in a highly efficient and concise manner, which features an efficient palladium-catalyzed enantioselective dearomative cyclization-kinetic resolution cascade to install the chiral all-carbon quaternary center, an effective sterically hindered Stille coupling, a powerful 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation to furnish all requisite unsaturation, and a tandem hydrolysis-ring closure sequence.

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