Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 7, Pages 3007-3016Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02891
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- Ministry of Science and Technology in Taiwan [MOST 103-2113-M-039-004]
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Spiro bis-C,C-alpha-arylglycosides were synthesized in three steps in 78-85% overall yields starting from exo-glycals. The initial Heck type C-aryl addition of exo-glycals with arylboronic acids afforded alpha-aryl-beta-substituted C-glycosides with exclusive alpha-stereoselectivity. Among the products, beta-ethanal alpha-aryl C-glycosides further reacted with alkylthiol in the presence of InCl3, followed by in situ Friedel-Crafts cyclization to yield the desirable final products. We proposed a mechanism to explain how the alpha-aryl group serves as a main determinant of the cyclization.
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