The stereoselective construction of E- and Z-Delta-Ile from E-dehydroamino acid ester: the synthesis of the phomopsin A tripeptide side chain

The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy) carbonyl)amino)-2-(diphenoxyphosphoryl) acetate as a common synthetic precursor for the synthesis of E-Delta-dehydroisoleucine and E-Delta-aspartate.

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 52; no. 7; pp. 1478 - 1481
Main Authors Yasuno, Yoko, Nishimura, Akito, Yasukawa, Yoshifumi, Karita, Yuma, Ohfune, Yasufumi, Shinada, Tetsuro
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 25.01.2016
Subjects
Amino Acids - chemistry
Chemistry
Chemistry, Multidisciplinary
Esters - chemistry
Mycotoxins - chemical synthesis
Mycotoxins - chemistry
Oligopeptides - chemical synthesis
Physical Sciences
Proton Magnetic Resonance Spectroscopy
Science & Technology
ELUCIDATION
CHEMICAL BIOLOGY
PEPTIDES
AMINO-ACIDS
NATURAL-PRODUCTS
CONFIGURATION
LEPTOSTROMIFORMIS
IDENTIFICATION
DERIVATIVES
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Summary:The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy) carbonyl)amino)-2-(diphenoxyphosphoryl) acetate as a common synthetic precursor for the synthesis of E-Delta-dehydroisoleucine and E-Delta-aspartate.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc08458j