Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 19, Pages 9740-9766Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01844
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Funding
- National Institute of General Medical Sciences [R01 GM084927]
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An enantioselective synthesis of the indole diterpenoid natural product paspaline is disclosed. Critical to this approach was the implementation of stereoselective desymmetrization reactions to assemble key stereocenters of the molecule. The design and execution of these tactics are described in detail, and a thorough analysis of observed outcomes is presented, ultimately providing the title compound in high stereopurity. This synthesis provides a novel template for preparing key stereocenters in this family of molecules, and the reactions developed en route to paspaline present a series of new synthetic disconnections in preparing 7steroidal natural products.
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