Total synthesis of norbadione A.
A short, convergent synthesis of the mushroom pigment norbadione A is described. The construction of an appropriately substituted naphtholactone intermediate involved a regioselective Diels-Alder reaction between a bis(triisopropylsilyloxy)diene and 2,6-dichlorobenzo-1,4-quinone. A double Suzuki-Miyaura cross-coupling between a diboronate and two identical enol triflates was another key feature of the synthesis.
Bourdreux
Yann
Y
CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, Bât. 547, 91191, Gif-sur-Yvette, France.
Nowaczyk
Stéphanie
S
Billaud
Célia
C
Mallinger
Aurélie
A
Willis
Catherine
C
Murr
Marine Desage-El
MD
Toupet
Loïc
L
Lion
Claude
C
Gall
Thierry Le
TL
Mioskowski
Charles
C
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D010648:Phenylacetates / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D010648:Phenylacetates; C464564:norbadione A; D015107:4-Butyrolactone