Ontology highlight
ABSTRACT:
SUBMITTER: Sharpe RJ
PROVIDER: S-EPMC4409926 | biostudies-literature | 2015 Apr
REPOSITORIES: biostudies-literature
Sharpe Robert J RJ Johnson Jeffrey S JS
Journal of the American Chemical Society 20150409 15
A stereocontrolled total synthesis of the indole diterpenoid natural product paspaline is described. Key steps include a highly diastereoselective enzymatic desymmetrization, substrate-directed epoxidation, Ireland-Claisen rearrangement, and diastereotopic group selective C-H acetoxylation to assemble the target with excellent stereofidelity. The route and results described herein outline complementary conceptual disconnections in the arena of steroid natural product synthesis. ...[more]