898546-99-1Relevant articles and documents
Stereocontrolled syntheses of (-)- And (+)-γ-diisoeugenol along with optically active eight stereoisomers of 7,8′-epoxy-8,7′-neolignan
Takubo, Tatsuaki,Kikuchi, Nao,Nishiwaki, Hisashi,Yamauchi, Satoshi
supporting information, p. 2168 - 2176 (2021/03/26)
It was shown that reduction of the tertiary benzylic hydroxy group of (2R,3S,4R,5S)-3,5-bis(4-benzyloxy-3-methoxyphenyl)-2,4-dimethyltetrahydro-3-furanol 17 followed by the intramolecular Friedel-Crafts reaction gave exclusively indane with (7S,7′S,8R,8′R)-2,7′-cyclo-7,8′-neolignan structure 18 along with (7S,7′R,8S,8′R)-7,8′-epoxy-8,7′-neolignan structure 19. Indane 18 was converted to (-)-γ-diisoeugenol ((-)-4). On the other hand, (2S,3R,4R,5S)-3,5-bis(4-benzyloxy-3-methoxyphenyl)-2,4-dimethyltetrahydro-3-furanol 22 did not afford indane, but the tetrahydrofuran structure with (7S,7′S,8S,8′S)-7,8′-epoxy-8,7′-neolignan structure 23 and 7′-epi-23.
Asymmetric synthesis of (+)-machilin f by unusual stereoselective mitsunobu reaction
Harada, Kenichi,Kubo, Naoko,Tanabe, Kazuma,Kubo, Miwa,Esumi, Tomoyuki,Hioki, Hideaki,Fukuyama, Yoshiyasu
, p. 1127 - 1132 (2011/05/05)
First synthesis of (+)-machilin F (1c) has been achieved in 16 steps as part of systematic synthetic studies on (-)-talaumidin (1) and its stereoisomers. The 2,3,4,5-tetrasubstituted tetrahydrofuran with the (2S,3S,4S,5S)-configuration has been constructe
