Catalytic enantioselective intramolecular Tishchenko reaction of meso-dialdehyde: synthesis of (S)-cedarmycins

Ismiyarto; Nobuki Kishi; Yuki Adachi; Rui Jiang; Takahiro Doi; Da-Yang Zhou; Kaori Asano; Yasushi Obora; Takayoshi Suzuki; Hiroaki Sasai; Takeyuki Suzuki

doi:10.1039/D1RA00915J

Catalytic enantioselective intramolecular Tishchenko reaction of meso-dialdehyde: synthesis of (S)-cedarmycins†

Ismiyarto,^a Nobuki Kishi,^b Yuki Adachi,^a Rui Jiang,^a Takahiro Doi,^a Da-Yang Zhou,^a Kaori Asano,^a Yasushi Obora,

^b Takayoshi Suzuki,^a Hiroaki Sasai^a and Takeyuki Suzuki

*^a

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* Corresponding authors

^a The Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki, Osaka 567-0047, Japan
E-mail: suzuki-t@sanken.osaka-u.ac.jp

^b Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials, and Bioengineering, Kansai University, Suita, Osaka 564-8680, Japan

Abstract

The first successful example of a catalytic enantioselective intramolecular Tishchenko reaction of a meso-dialdehyde in the presence of a chiral iridium complex is described. Chiral lactones were obtained in good yields with up to 91% ee. The obtained enantioenriched lactones were utilized for the first synthesis of (S)-cedarmycins A and B.

RSC Advances

Catalytic enantioselective intramolecular Tishchenko reaction of meso-dialdehyde: synthesis of (S)-cedarmycins†

Abstract

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