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Syntheses of all eight stereoisomers of conidendrin.
- Source :
-
Bioscience, Biotechnology & Biochemistry . Oct2020, Vol. 84 Issue 10, p1986-1996. 11p. - Publication Year :
- 2020
-
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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 09168451
- Volume :
- 84
- Issue :
- 10
- Database :
- Academic Search Index
- Journal :
- Bioscience, Biotechnology & Biochemistry
- Publication Type :
- Academic Journal
- Accession number :
- 145623696
- Full Text :
- https://doi.org/10.1080/09168451.2020.1777081