Synthesis of 1,2-Oxygenated 6-arylfurofuran Lignan: Stereoselective Synthesis of (1S,2S,5R,6S)-1-hydroxysamin | Zendy

Satoshi Yamauchi | Zendy; Satoshi Bando | Zendy; Yoshiro Kinoshita | Zendy

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Synthesis of 1,2-Oxygenated 6-arylfurofuran Lignan: Stereoselective Synthesis of (1S,2S,5R,6S)-1-hydroxysamin

Author(s) -

Satoshi Yamauchi,

Satoshi Bando,

Yoshiro Kinoshita

Publication year - 2002

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.66.1495

Subject(s) - stereoselectivity , aldehyde , hydroxylation , lignan , chemistry , olefin fiber , diol , stereochemistry , organic chemistry , catalysis , enzyme

(1S,2S,5R,6S)-6-(3,4-Methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octan-1,2-diol ((+)-1-hydroxysamin 1) was synthesized, starting from olefin 8. Stereoselective alpha-hydroxylation was achieved after converting 8 to aldehyde 13. Resulting unstable alpha-hydroxy aldehyde 14 was then transformed to (+)-1-hydroxysamin (1). This is a new efficient synthetic route to 1,2-oxygenated 6-arylfurofuran lignans.

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