Enantioselective syntheses of pachastrissamine and jaspine A via hydroxylactonization of a chiral epoxy ester
| Autor: | Masaru Enomoto, Hiroyuki Urano, Shigefumi Kuwahara |
|---|---|
| Rok vydání: | 2010 |
| Předmět: |
Oxazolidine
Stereochemistry Epoxide Ring (chemistry) Applied Microbiology and Biotechnology Biochemistry Aldehyde Analytical Chemistry Substrate Specificity chemistry.chemical_compound Lactones Sphingosine Organic chemistry Molecular Biology chemistry.chemical_classification Chemistry Organic Chemistry Enantioselective synthesis Total synthesis Esters Stereoisomerism General Medicine Bridged Bicyclo Compounds Heterocyclic Cyclization Yield (chemistry) Intramolecular force Epoxy Compounds Biotechnology |
| Zdroj: | Bioscience, biotechnology, and biochemistry. 74(1) |
| ISSN: | 1347-6947 |
| Popis: | A new enantioselective total synthesis of pachastrissamine (jaspine B) was achieved from a known alpha,beta-unsaturated aldehyde by utilizing Córdova's asymmetric epoxidation as the chirality-inducing step. The 2,3-cis stereochemistry of pachastrissamine was established via intramolecular epoxide ring opening of a gamma,delta-epoxy-alpha,beta-unsaturated ester intermediate coupled with oxy-Michael cyclization. Treatment of pachastrissamine with tetrahydro-2-furanol under acidic conditions led to smooth oxazolidine ring formation, furnishing jaspine A in a high yield. |
| Databáze: | OpenAIRE |
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