Total synthesis of (–)–6–epi–hygrophorones B14 and (–)–4–epi–hygrophorone D14 was achieved using stereoselective Grignard reaction, Bernet–Vasella protocol and Ring closing metathesis, starting from D–mannose.
Uvacalols are novel carbasugars isolated from the genera Uvaria. In this study, we report concise syntheses of (1R,2S,3R,6R)-6-ethoxy-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol, a key intermediate for the synthesis of uvacalols I and J, and of its epimer (1R,2S,3S,6R)-6-ethoxy-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol, starting from cheap and readily available methyl d-glucopyranoside.
This review reports on the total synthesis of conduramines, which are formally derived from conduritols, these molecules are mainly contains trihydroxy aminocyclohexene core. Analysis of the different strategies developed to prepare these aminocyclohexene triols and their derivatives has been carried out with special attention paid to the methods employed for the insertion of chiral amine moiety.
Stereoselective and short approach for synthesis of some carbahexopyranoses namely, MK7607, (−)-gabosine A, (−)-conduritol E, (−)-conduritol F, 6a-carba-β-d-fructopyranose and other carbasugars using chemoselective Grignard or NHTK reactions and RCM.
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