TY - JOUR
T1 - Total Synthesis of Terpioside B
AU - Inaba, Kazuki
AU - Endo, Masato
AU - Iibuchi, Naoto
AU - Takahashi, Daisuke
AU - Toshima, Kazunobu
N1 - Funding Information:
This research was supported in part by the JSPS KAKENHI Grant Number JP19H02724 in Scientific Research (B) and a SUNBOR Grant from the Suntory Foundation for Life Sciences.
Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2020/8/12
Y1 - 2020/8/12
N2 - The first total synthesis of terpioside B (1) has been accomplished. Key steps include the stereoselective installments of a set of challenging 1,2-cis-glycosidic linkages. Thus, α(1,4)-linked d-galactoside was effectively constructed from a 1,2-anhydrogalactose donor and an unprotected 1,6-anhydrogalactose acceptor by using a boron-mediated aglycon delivery (BMAD) method. In addition, α-l-fucofuranosides were stereoselectively and simultaneously constructed by remote group-assisted 1,2-cis-α-stereoselective glycosylations.
AB - The first total synthesis of terpioside B (1) has been accomplished. Key steps include the stereoselective installments of a set of challenging 1,2-cis-glycosidic linkages. Thus, α(1,4)-linked d-galactoside was effectively constructed from a 1,2-anhydrogalactose donor and an unprotected 1,6-anhydrogalactose acceptor by using a boron-mediated aglycon delivery (BMAD) method. In addition, α-l-fucofuranosides were stereoselectively and simultaneously constructed by remote group-assisted 1,2-cis-α-stereoselective glycosylations.
KW - boron-mediated aglycon delivery
KW - glycosphingolipids
KW - glycosylation
KW - terpioside B
KW - total synthesis
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U2 - 10.1002/chem.202002878
DO - 10.1002/chem.202002878
M3 - Article
C2 - 32567165
AN - SCOPUS:85087790202
SN - 0947-6539
VL - 26
SP - 10222
EP - 10225
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 45
ER -