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- Title
Syntheses of all eight stereoisomers of conidendrin.
- Authors
Shirakata, Hinako; Nishiwaki, Hisashi; Yamauchi, Satoshi
- Abstract
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. All stereoisomers of conidendrin with 97-100%ee were synthesized from common starting materials and its enantiomers with epimerization.
- Subjects
STEREOISOMERS; ENANTIOMERIC purity; FRIEDEL-Crafts reaction; EPIMERIZATION; DIASTEREOISOMERS
- Publication
Bioscience, Biotechnology & Biochemistry, 2020, Vol 84, Issue 10, p1986
- ISSN
0916-8451
- Publication type
Article
- DOI
10.1080/09168451.2020.1777081