A domino-based approach toward stereodefined heavily functionalized cyclohexanes: synthesis of iridal's core structure.
A stereoselective synthesis of heavily functionalized six-membered ring subunits, which possess functionality at sites appropriate for further elaboration, is described. The cyclopentanone moiety of hydrindenediol is required to achieve total facial selectivity during the pre-domino installation of the second quaternary center, while oxidative cleavage is responsible for the ring-expanding rearrangement. A microwave-assisted version of the key domino transformation and a test of concept approach toward the iridal core structure are also presented.
Corbu
Andrei
A
Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, Gif-sur-Yvette, France.
Gauron
Guillaume
G
Castro
Juan M
JM
Dakir
Mohamed
M
Arseniyadis
Siméon
S
D003510:Cyclohexanes / Q000138:chemical synthesis / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry*
D003510:Cyclohexanes; D014315:Triterpenes; C473636:iridal; D010100:Oxygen