A Stereodivergent Approach for Accessing Both C2,8a-Syn and C2,8a-Anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCL(4)-Promoted Aza-[3 + 3] Annulation.
Details in developing a stereodivergent approach to the lepadin family and establishing an entry to both C2,8a-syn and C2,8a-anti relative stereochemical manifolds through a common intermediate are described here. This works paves a foundation for constructing all members of the lepadin family, which consists of three subsets based on an array of interesting relative configurations. These efforts underline the prominence of aza-[3 + 3] annulation as a unified strategy in alkaloid synthesis.
Li
Gang
G
Division of Pharmaceutical Sciences and Department of Chemistry, Wisconsin Center for Natural Products Research, School of Pharmacy, Rennebohm Hall, University of Wisconsin, Madison, WI 53705.
Carlson
Lauren J
LJ
Sagamanova
Irina K
IK
Slafer
Brian W
BW
Hsung
Richard P
RP
Gilardi
Claudio
C
Sklenicka
Heather M
HM
Sydroenko
Nadiya
N