Synthesis of anemoclemoside B, the first natural product with an open-chain cyclic acetal glycosidic linkage

Organic Letters

Volumn 7, Issue 10, 2005, Pages 1935-1938

  Sun, Jiansong ^b   Han, Xiuwen ^b   Yu, Biao ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; ANEMOCLEMOSIDE B; GLYCOSIDE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; SYNTHESIS;

ACETALS; BIOLOGICAL PRODUCTS; GLYCOSIDES; MEDICINE, CHINESE TRADITIONAL; PLANT ROOTS; PLANTS, MEDICINAL;

EID: 19544371385     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050324y     Document Type: Article

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26. Acetal 14a was transformed into the corresponding 2,3,2′,3′, 4′,5′-hexa-O-acetyl derivative 19 via hydrogenolysis and acetylation (see Supporting Information), which provided diagnostic NOE correlations between the 1′-H and the 4-H and 6-H, thus confirming the 1′R configuration in 14a. Similarly, compound 15 was converted into the corresponding 2,2″,3,3′,3″,4′,4″,5′-octa-O- acetyl derivative 20 (see Supporting Information). Compound 20 provided diagnostic NOE correlations between the 1′-H and the 4-H and 6-H.
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28. For the preparation and characterization of all compounds mentioned in the context, see Supporting Information.