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Total Synthesis of (−)‐Bauhinin
Author(s) -
JosienLefebvre Delphine,
Desmares Guillaume,
Drian Claude Le
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20010418)84:4<890::aid-hlca890>3.0.co;2-q
Subject(s) - chemistry , aglycone , yield (engineering) , reagent , total synthesis , wittig reaction , bromide , derivative (finance) , hydrogen bromide , photoisomerization , organic chemistry , stereochemistry , isomerization , glycoside , bromine , catalysis , materials science , economics , financial economics , metallurgy
The total synthesis of the naturally occurring cyanoglucoside (−)‐bauhinin ( 1 ) was achieved starting from the optically pure oxatrinorbornenone 2 in 12 steps and 8% overall yield. The aglycone of (−)‐bauhinin was easily obtained from the optically pure oxatrinorbornenone derivative 6 by a Wittig‐Horner reaction followed by the opening of the oxa bridge. Glycosidation with tetra‐ O ‐isobutyryl‐ D ‐glucosyl bromide 9 as the reagent in the Koenigs‐Knorr reaction afforded glucoside 10 in 58% yield, which, after photoisomerization and deprotection, gave (−)‐bauhinin ( 1 ).