TY - JOUR
T1 - Highly Stereocontrolled Synthesis of 2,6-Dideoxy Sugars and its Application to Synthesis of Natural Products
AU - Toshima, Kazunobu
AU - Tatsuta, Kuniaki
PY - 1992
Y1 - 1992
N2 - Novel methodologies for stereocontrolled synthesis of 2,6-dideoxy sugars by efficient use of 2,6-anhydro-2-thio sugar and its application to synthesis of natural products are described. This article involves highly stereocontrolled and powerful glycosylations of 2,6-anhydro-2-thio sugar for synthesis of 2,6-dideoxy-α- and β-glycosides and highly sterecontrolled creations of C-3 configuration of 2,6-dideoxy sugar by an addition of a nucleophilic reagent to 2,6-anhydro-2-thio sugar. Further, the efficient total synthesis of erythromycin A, which is a most typical and clinically important macrolide antibiotic, from (9S)-9-dihydroerythronolide A is achieved by the successful application of the present novel methodologies.
AB - Novel methodologies for stereocontrolled synthesis of 2,6-dideoxy sugars by efficient use of 2,6-anhydro-2-thio sugar and its application to synthesis of natural products are described. This article involves highly stereocontrolled and powerful glycosylations of 2,6-anhydro-2-thio sugar for synthesis of 2,6-dideoxy-α- and β-glycosides and highly sterecontrolled creations of C-3 configuration of 2,6-dideoxy sugar by an addition of a nucleophilic reagent to 2,6-anhydro-2-thio sugar. Further, the efficient total synthesis of erythromycin A, which is a most typical and clinically important macrolide antibiotic, from (9S)-9-dihydroerythronolide A is achieved by the successful application of the present novel methodologies.
KW - (9 S)-9-Dihydroerythronolide A
KW - 2,6-Anhydro-2-thio sugar
KW - 2,6-Dideoxy sugar
KW - Erythromycin A
KW - Stereocontrolled glycosylation
KW - Stereocontrolled nucleophilic addition
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U2 - 10.5059/yukigoseikyokaishi.50.303
DO - 10.5059/yukigoseikyokaishi.50.303
M3 - Article
AN - SCOPUS:85022794070
VL - 50
SP - 303
EP - 315
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
SN - 0037-9980
IS - 4
ER -