Total synthesis of gracilioether F. Development and application of Lewis acid promoted ketene–alkene [2+2] cycloadditions and late-stage C—H oxidation
Journal Article
·
· Angewandte Chemie (International Edition)
- Indiana Univ., Bloomington, IN (United States)
The first synthesis of gracilioether F, a polyketide natural product with an unusual tricyclic core and five contiguous stereocenters, is described. Key steps of the synthesis include a Lewis acid promoted ketene–alkene [2+2] cycloaddition and a late-stage carboxylic acid directed C(sp³)—H oxidation. The synthesis requires only eight steps from norbornadiene.
- Research Organization:
- Argonne National Lab. (ANL), Argonne, IL (United States)
- Sponsoring Organization:
- USDOE
- OSTI ID:
- 1171255
- Journal Information:
- Angewandte Chemie (International Edition), Vol. 53, Issue 52; ISSN 1433-7851
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- ENGLISH
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