Synthetic studies on the bioactive tetramic acid JBIR-22 using a late stage Diels-Alder reaction.
A late stage Diels-Alder reaction is used to prepare a mixture of JBIR-22, a natural product from the Equisetin family of tetramic acids, and one of its diastereomers. This is achieved in just 8 steps from pyruvate. The success of the late stage DA approach is discussed in the context of the biosynthesis of JBIR-22 (and perhaps related natural products).
School of Chemistry & Biomedical Sciences Research Complex, University of St Andrews & EaStCHEM, North Haugh, St Andrews, KY16 9ST, UK. njw3@st-andrews.ac.uk.
A R
AR
Healy
N J
NJ
Westwood
D003500:Cyclization; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
C549607:JBIR-22; D009281:Naphthalenes; D011760:Pyrrolidinones; D013764:Tetrahydronaphthalenes; C009435:tetramic acid; C024509:equisetin; C007229:decalin