Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5271572 | Tetrahedron Letters | 2013 | 4 Pages |
Abstract
A fully stereoselective preparation of the advanced intermediate 24 for the synthesis of (+)-lactacystin from known 1,2:5,6-di-O-isopropylidene-α-d-gulofuranose (2), as the source of chirality, has been achieved. The C-5 methyl group was introduced via a Wittig olefination followed by Pd/C-mediated hydrogenation of the conformationally restricted alkene 11 in a highly stereoselective manner. The stereogenic tetrasubstituted carbon centre at C-3, with an amino group, was installed stereoselectively via an Overman rearrangement, which was efficiently controlled by a saccharide environment.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Jozef Gonda, Dávid MaliÅák, Margaréta KováÄová, Miroslava Martinková,