TY - JOUR
T1 - Construction of 2,6,9,11-tetraoxatricyclo[6.2.1.03,8]undecane containing 4-keto-D-glucose skeleton
AU - Fujitani, Ban
AU - Hanaya, Kengo
AU - Higashibayashi, Shuhei
AU - Shoji, Mitsuru
AU - Sugai, Takeshi
N1 - Funding Information:
This work was supported by JSPS KAKENHI (Grant Number 17K01952 ) and acknowledged with thanks.
PY - 2017/12/21
Y1 - 2017/12/21
N2 - A unique tricyclic bisacetal, 2,6,9,11-tetraoxatricyclo[6.2.1.03,8]undecane observed in cotylenin A, was constructed in a simplified model compound, based on 6-O-methyl-4-keto-D-glucose as the scaffold to control of the stereochemistry. The key compound was an unprecedented spirolactone formed from the α-(α′-hydroxy)acyloxy dimethyl acetal, accompanied with stereoselective migration of an acyl group. Subsequent intramolecular acetalization between the hydroxy group at the C-3 and the C-1′ hemiacetal position furnished the desired tricyclic bisacetal.
AB - A unique tricyclic bisacetal, 2,6,9,11-tetraoxatricyclo[6.2.1.03,8]undecane observed in cotylenin A, was constructed in a simplified model compound, based on 6-O-methyl-4-keto-D-glucose as the scaffold to control of the stereochemistry. The key compound was an unprecedented spirolactone formed from the α-(α′-hydroxy)acyloxy dimethyl acetal, accompanied with stereoselective migration of an acyl group. Subsequent intramolecular acetalization between the hydroxy group at the C-3 and the C-1′ hemiacetal position furnished the desired tricyclic bisacetal.
KW - 4-Ketoglucoside
KW - Acyl migration
KW - Cotylenin A
KW - Natural product synthesis
KW - Spirolactone
KW - Tricyclic bisacetal
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U2 - 10.1016/j.tet.2017.11.008
DO - 10.1016/j.tet.2017.11.008
M3 - Article
AN - SCOPUS:85034740107
SN - 0040-4020
VL - 73
SP - 7217
EP - 7222
JO - Tetrahedron
JF - Tetrahedron
IS - 51
ER -