Syntheses of all eight stereoisomers of conidendrin.

Hinako Shirakata, Hisashi Nishiwaki, Satoshi Yamauchi

Bioscience, biotechnology, and biochemistry 2020 Oct

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All eight stereoisomers of conidendrin were synthesized from (1 R,2 S,3 S)-1-(4-benzyloxy-3-methoxyphenyl)-3-(4-benzyloxy-3-methoxybenzyl)-2- hydroxymethyl-1,4-butanediol ((+)-4) and its enantiomer with high optical purity. The configurations at 4-positions of the conidendrin stereoisomers were constructed by intramolecular Friedel-Crafts reaction of protected 4. After conversion to tetrahydronaphthalene intermediate 7a, the 2- and 3-position of tetrahydronaphthalene structure 7a were converted to 3a- and 9a-position of (+)-α-conidendrin (3a), respectively. By the epimerization process of 2- or 3-position of 7a, the other diastereomers were obtained. All enantiomers were also synthesized from (-)-4.

Citation

Hinako Shirakata, Hisashi Nishiwaki, Satoshi Yamauchi. Syntheses of all eight stereoisomers of conidendrin. Bioscience, biotechnology, and biochemistry. 2020 Oct;84(10):1986-1996