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. 2010 Jul 2;12(13):2986-9.
doi: 10.1021/ol101009q.

Synthesis of SL0101 carbasugar analogues: carbasugars via Pd-catalyzed cyclitolization and post-cyclitolization transformations

Mingde Shan  1 , George A O'Doherty
Affiliations

Synthesis of SL0101 carbasugar analogues: carbasugars via Pd-catalyzed cyclitolization and post-cyclitolization transformations

Mingde Shan et al. Org Lett. .

Abstract

A general approach to the stereoselective synthesis of 5a-carbasugars has been developed. The route mimics our palladium-catalyzed glycosylation/postglycosylation approach to carbohydrates in that it also utilizes a highly regio- and stereospecific palladium-catalyzed allylation and postglycosylation reaction sequence for the installation of either D- or L-cyclitols. This cyclitolization/postcyclitolization sequence was used for the enantioselective synthesis of a cyclitol analogue of SL0101, its D-sugar enantiomer, as well as several acetylation pattern analogues.

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Figures

Figure 1
Figure 1
RSK2 inhibitors SL0101 and its analogues
Scheme 1
Scheme 1
De Novo Approach to normal sugar and carbasugar
Scheme 2
Scheme 2
Synthesis of two α-Boc-enones from quinic acid
Scheme 3
Scheme 3
Pd-Cyclitolization for α-Boc-enones with BnOH
Scheme 4
Scheme 4
Post-cyclitolization transformation
Scheme 5
Scheme 5
Pd-Cyclitolization for kaempferol with α-l-Boc-enone
Scheme 6
Scheme 6
Synthesis of SL0101 5a-carbasugar α-l-glycoside 4
Scheme 7
Scheme 7
Synthesis of SL0101 5a-carbasugar α-l-glycoside 5 & 6
Scheme 8
Scheme 8
Synthesis of (ent)-6
Scheme 9
Scheme 9
Synthesis of (ent)-5 & (ent)-4
See this image and copyright information in PMC

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