TY  - JOUR
A1  - Otte, Fabian
A1  - Schmidt, Bernd
T1  - Matsuda-Heck Arylation of Glycals for the Stereoselective Synthesis of Aryl C-Glycosides
T2  - The journal of organic chemistry
N2  - The methoxymethyl-protected glycal L-amicetal, synthesized de novo from L-ethyl lactate through tandem ring-closing metathesis-isomerization sequence, undergoes a highly trans-diastereoselective Heck-type coupling reaction with various arene diazonium salts to furnish 2,3-unsaturated aryl C-glycosides in moderate to excellent yields. The products can be further functionalized, e.g., by hydrogenation, epoxidation, or dihydroxylation to furnish 2,3,6-tridesoxy, 2,3-anhydro-6-desoxy, or 6-desoxy aryl C-glycosides, respectively. The method was applied to the synthesis of an a-configured 6-desoxy-gliflozin derivative.
Y1  - 2019
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/47838
SN  - 0022-3263
SN  - 1520-6904
VL  - 84
IS  - 22
SP  - 14816
EP  - 14829
PB  - American Chemical Society
CY  - Washington
ER  -