Construction of Optically Active Isotwistanes and Aminocyclitols Using Chiral Cyclohexadiene as a Common Intermediate

Shinji Harada; Kexin Li; Ryuto Kino; Takuya Takeda; Chia-Hsien Wu; Shiharu Hiraoka; Atsushi Nishida

doi:10.1248/cpb.c16-00431

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Construction of Optically Active Isotwistanes and Aminocyclitols Using Chiral Cyclohexadiene as a Common Intermediate

Shinji Harada, Kexin Li, Ryuto Kino, Takuya Takeda, Chia-Hsien Wu, Shiharu Hiraoka, Atsushi Nishida

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Keywords: isotwistane, homoisotwistane, aminocyclitol, Diels–Alder, asymmetric catalysis, hetero-Diels–Alder

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2016 Volume 64 Issue 10 Pages 1474-1483

DOI https://doi.org/10.1248/cpb.c16-00431

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Abstract

We have developed a new method for synthesizing chiral isotwistane and homoisotwistane skeletons as well as aminocyclitols in a highly stereoselective manner. These results were achieved through the use of a common intermediate, which was derived from the ytterbium-catalyzed asymmetric Diels–Alder reaction of Danishefsky diene.

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