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Synthesis of (−)-Conduritol C (1L-Cyclohex-5-ene-1,2,3/4-tetrol)

✍ Scribed by Claude Le Drian; Eric Vieira; Pierre Vogel

Publisher
John Wiley and Sons
Year
1989
Tongue
German
Weight
749 KB
Volume
72
Category
Article
ISSN
0018-019X

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✦ Synopsis

2, 3, 4, Enantiomerically pure 7-oxabicyclo[2.2.l]hept-5-en-2-yl derivatives ('naked sugars' [I]) as synthetic intermediates, Part VI; Part V: [2]. Present address: Ciba-Geigy SA, Marly, CH-1700 Fribourg. For recent syntheses, see conduritol A [8], (i)-conduritol B [9] [lo], (*)-tetra-0-henzylconduritol B [l I], (*)-I ,2-di-0-benzoyl-4-O-methylconduritol F [12], and (i)-anhydroconduritols [ 131.

For the determination of the absolute configuration of the cyclohexanetetrols, see [16] [17].

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## Abstract The ‘naked sugar’ (+)‐(1__R__,2__R__4__R__)‐2‐__endo__‐cyano‐7‐oxabicyclo[2.2.1]hept‐5‐sn‐2‐__exo__‐yl acetate ((+)‐4) was converted (7 steps, 45% overall) with high stereoselectivity into (−)‐(4__R__,5__S__,6__R__)‐4,5,6‐tris{[(__tert__‐butyl)dimethylsilyl]oxy}cyclohex‐2‐en‐1‐one ((−)‐

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The configurations of 1 and 2 were tentatively assigned [2] on the relative rates of dehydrobromination with sodium ethoxide and on the conversion [l] of one of them into a previously described [ 31 triacetate.