TY - JOUR
T1 - Stereoselective synthesis of highly functionalized C-glycosides based on acetal [1,2] and [1,4] Wittig rearrangements
AU - Tomooka, Katsuhiko
AU - Yamamoto, Hiroshi
AU - Nakai, Takeshi
PY - 2000/12/15
Y1 - 2000/12/15
N2 - Two types of highly functionalized C-glycosides were stereoselectively synthesized from an ethynylvinyl-methanol-derived O-glycoside in one step through acetal Wittig rearrangements (see scheme). The [1,2] Wittig rearrangement affords the 1β-C-glycoside that has contiguous quarternary chiral centers at the C1 and C1′ positions, while the [1,4] Wittig rearrangement has been used for the first time in the synthesis of C-glycosides.
AB - Two types of highly functionalized C-glycosides were stereoselectively synthesized from an ethynylvinyl-methanol-derived O-glycoside in one step through acetal Wittig rearrangements (see scheme). The [1,2] Wittig rearrangement affords the 1β-C-glycoside that has contiguous quarternary chiral centers at the C1 and C1′ positions, while the [1,4] Wittig rearrangement has been used for the first time in the synthesis of C-glycosides.
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U2 - 10.1002/1521-3773(20001215)39:24<4500::AID-ANIE4500>3.0.CO;2-W
DO - 10.1002/1521-3773(20001215)39:24<4500::AID-ANIE4500>3.0.CO;2-W
M3 - Article
AN - SCOPUS:0034671723
SN - 1433-7851
VL - 39
SP - 4500
EP - 4502
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 24
ER -