Torsional steering controls the stereoselectivity of epoxidation in the guanacastepene a synthesis.
[reaction: see text] The stereoselectivity of the key epoxidation step in the synthesis of guanacastepene A is shown to be controlled by torsional steering. In this particular epoxidation reaction, the transition structure energetic difference is enhanced by the great asynchronicity of the forming C-O bonds that intensifies the torsional interactions.
Cheong
Paul Ha-Yeon
PH
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Yun
Heedong
H
Danishefsky
Samuel J
SJ
Houk
K N
KN
D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D004224:Diterpenes; C409194:guanacastepene