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Total Syntheses of (−)-Conduritol B ((−)-1L-Cyclohex-5-ene-1,3/2,4-tetrol) and of (+)-Conduritol F((+)-1D-Cyclohex-5-ene-1,2,4/3-tetrol). Determination of the Absolute Configuration of (+)-Leucanthemito

✍ Scribed by Claude Le Drian; Jean-Paul Vionnet; Pierre Vogel

Publisher
John Wiley and Sons
Year
1990
Tongue
German
Weight
585 KB
Volume
73
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 ((−)‐11). Reduction of (−)‐1 with NaBH~4~‐ CeCl~3~ · 7 H~2~O, followed by deprotection of the silyl ether moieties gave (+)‐conduritol F ((+)‐1; 47%) whose characteristics were identical to those of natural (+)‐leucanthemitol. Reduction of (−)‐11 with DIBAH, followed by deprotection of the silyl ether moiety led to (−)‐conduritol B ((−)‐3; 51 %).

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