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Synlett 2011(9): 1318-1320  
DOI: 10.1055/s-0030-1260547
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Short and Efficient Syntheses of Gabosine I, Streptol, 7-O-Acetylstreptol, 1-epi-Streptol, Gabosine K, and Carba-α-d-glucose from δ-d-Gluconolactone

Tony K. M. Shing*, Y. Chen, W. L. Ng
Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, Hong Kong, P. R. of China
Fax: +85226035057; e-Mail: tonyshing@cuhk.edu.hk;
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Publication History

Received 10 February 2011
Publication Date:
29 April 2011 (online)

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Abstract

δ-d-Gluconolactone was carbocyclized into an EOM-protected cyclohexenone in four steps involving perethoxymethylation, phosphonate anion addition, reduction, and oxidation with concomitant Horner-Wadsworth-Emmons alkenation. The stable key enone was efficiently transformed into gabosine I (five steps with 65% overall yield from δ-d-gluconolactone), streptol (six steps, 54% overall yield), 7-O-acetyl-streptol (seven steps, 42% overall yield), 1-epi-streptol (six steps, 49% overall yield), gabosine K (seven steps, 40% overall yield), and carba-α-d-glucopyranose (seven steps, 47% overall yield). The present chemical syntheses, from commercially available δ-d-gluconolactone, provide the highest overall yields of these molecules to date.

Key words

carbasugars - carbohydrates - stereoselective synthesis - Wittig reaction - natural products

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