Acyclic Stereoselective Synthesis of Carbohydrates

Synthetic Applications of 1-Aminoalkyl Chloromethyl Ketones. Synthesis of Enantiopure 3-Azetidinols and Aminoalkyl Epoxides

“…Thus, in this paper, we report the preparation of enantiomerically pure 3-azetidinols in an efficient synthesis starting from 1-aminoalkyl chloromethyl ketones. We also report the generalization of the synthesis of α-amino epoxides, because of their synthetic usefulness, through the addition of organometallic compounds to 1-aminoalkyl chloromethyl ketones. In both cases, the addition of the organometallic compounds to the ketones takes place with high diastereoselectivity and full retention of the stereochemistry at the α-carbon of the starting α-amino ketone.…”

Concepts for the Total Synthesis of Deoxy Sugars

“…Although this synthetic approach is still widely used and often is very reliable for targeting selected deoxy sugars, concepts based on the total synthesis of deoxy sugars become more and more competitive or even superior. 11,12 The number of carbohydrates available as suitable starting materials is rather restricted so that lengthy syntheses are required to selectively remove hydroxy groups, incorporate new functional groups or branching points or to switch from the D-into the L-series ning and received his Ph.D. degree in 1998 by working on the total synthesis of ansamycin antibiotics. This was followed by a postdoctoral stay at the ETH Zürich and at the Scripps Research Institute (USA) working with Prof. A. Eschenmoser where he was involved in the synthesis and biological evaluation of unnatural oligonucleotides.…”

Stereoselective Preparation of Allylic Alcohol Intermediates in the Synthesis of Deoxysugars

“…1 In this context, the total synthesis of 2,6-dideoxy and 2,3,6-trideoxy-3-aminohexoses of the L series represents a major task in synthetic carbohydrate chemistry. 2 To this end we have been using extensively the C4 alde- In particular, with diallylzinc as the nucleophile, steric control by the two chiral centers embedded in the dioxolane system was remarkably high, homoallylic amines with antl stereochemistry between the a-oxygen and the newly formed chiral center being obtained as almost exclusive reaction products.…”