Stereoselective cascade reactions that incorporate a 7-exo acyl radical cyclization.
[reaction: see text] Radical cascades that feature a 7-exo acyl radical cyclization followed by a 6-exo or 5-exo alkyl radical cyclization proceed with very good yields and diastereoselectivities. Two stereocenters are created by the reaction, and a single isomeric product was obtained from each of the five substrates examined. The relative configurations of the products are consistent with cyclizations occurring via chairlike or pseudochairlike transition states.
Grant
Seth W
SW
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.
Zhu
Koudi
K
Zhang
Yu
Y
Castle
Steven L
SL
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000473:Alkanes / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D000473:Alkanes; D011083:Polycyclic Compounds; C435307:lyconadin A