Short and Efficient Synthesis of Cryptophycin Unit A
| Autor: | Hans-Georg Stammler, Beate Neumann, Markus Nahrwold, Norbert Sewald, Stefan Eissler |
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| Rok vydání: | 2007 |
| Předmět: |
Models
Molecular Aldehydes Mukaiyama aldol addition Molecular Structure Chemistry Stereochemistry Organic Chemistry Crystallography X-Ray Peptides Cyclic Biochemistry Catalysis Stereocenter Cryptophycin Dihydroxylation Depsipeptides Salt metathesis reaction Moiety Physical and Theoretical Chemistry Chirality (chemistry) |
| Zdroj: | Organic Letters. 9:817-819 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol063032l |
| Popis: | [reaction: see text] Two short synthetic approaches toward cryptophycin unit A comprise a catalytic asymmetric dihydroxylation as the sole source of chirality, while all further stereogenic centers are introduced under substrate control. The key step of the first route is a vinylogous Mukaiyama aldol addition, which introduces the alpha,beta-unsaturated ester moiety with defined configuration at the delta-carbon atom. Likewise, allylation with allyltributylstannane diastereoselectively gives the homoallylic alcohol that can be converted by a metathesis reaction to a unit A precursor. |
| Databáze: | OpenAIRE |
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