- Versatile use of bis-cyclic thionocarbonates of polyols as bis-electrophilic intermediates. Synthesis of polyhydroxylated thioanhydropentitols with D,L-arabino, L-ribo and L-xylo, and thioanhydroaldoses with D-lyxo, L-ribo, D-xylo, D-allo, D-gulo and D-al
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1-O-Benzylpentitols (with D-arabino, D-lyxo, D,L-xylo and D,L-ribo configurations) and aldose dibenzyldithioacetals (with L-arabino, D-lyxo, D-xylo, D-ribo, D-galacto, D-gluco and D-manno configurations) were directly and efficiently transformed into thei
- Danquigny, Alain,Benazza, Mohammed,Protois, Sylvain,Demailly, Gilles
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p. 4365 - 4369
(2007/10/03)
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- STEREOCONTROLLED SYNTHESIS OF A C14-C20 BUILDING BLOCK FOR AMPHOTERICIN B USING A NOVEL WITTIG REARRANGEMENT
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The C14-C20 unit 11 of the polyene macrolide antibiotic amphotericin B (1) was synthesized from L-arabinose in 13 steps.The key step 7 -> 10 features diastereocontrol through asymmetric induction in a novel Wittig rearrangement.
- Bruecker, Reinhard
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p. 5747 - 5750
(2007/10/02)
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- A Convenient Synthesis of Four Stereoisomers of 6-Acetoxy-5-hexadecanolide, the Major Component of the Mosquito Oviposition Attractant Pheromone
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The major component of the mosquito oviposition attractant pheromone (5S,6R)-(+)- and (5R,6S)-(-)-erythro-6-acetoxy-5-hexadecanolide and their threo-isomers, (5R,6R)-(+)- and (5S,6S)-(-)-6-acetoxy-5-hexadecanolide were synthesized from isopropylidene-D-glyceraldehyde and isopropylidene-L-glyceraldehyde, respectively, in which the nucleophilic addition of Grignard reagent involved the diastereoface-differentiating process as the key step.The bioassay of four erythro- and threo-isomers against mosquito (Culex pipiens molestus) was conducted. (5R,6S)-(-)-erythro-6-acetoxy-5-hexadecanolide proved to be the most effective as an attractant.
- Machiya, Kozo,Ichimoto,Itsuo,Kirihata, Mitsunori,Ueda, Hiroo
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p. 643 - 650
(2007/10/02)
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