Determination of the stereochemistry of the tetrahydropyran sesquineolignans morinols A and B.
The 7',8'-stereochemistry of the tetrahydropyran sesquineolignans morinols A and B was determined as threo via synthetic studies and by comparison of NMR data of 7',8'-threo-morinol and 7',8'-erythro-morinol. This study also confirmed that the biosynthetic process produces enantiomeric mixtures of morinols A and B. This was ascertained by comparing the specific rotations of synthesized morinols A and B with those of naturally occurring morinols A and B.
Yamauchi
Satoshi
S
Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan. syamauch@agr.ehime-u.ac.jp
Sugahara
Takuya
T
Akiyama
Koichi
K
Maruyama
Masafumi
M
Kishida
Taro
T
D017705:Lignans / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D019684:Magnoliopsida / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification
D017705:Lignans; D011714:Pyrans; C519741:morinol A; C519740:morinol B