1. Approaches to Polycyclic 1,4-Dioxygenated Xanthones. Application to Total Synthesis of the Aglycone of IB-00208
- Author
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Daniel Knueppel, Douglas Mans, Stephen F. Martin, Jingyue Yang, and Bo Cheng
- Subjects
Letter ,Stereochemistry ,Xanthones ,Diol ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Aldehyde ,chemistry.chemical_compound ,Glucosides ,Xanthone ,Salt metathesis reaction ,Organic chemistry ,Physical and Theoretical Chemistry ,Nuclear Magnetic Resonance, Biomolecular ,chemistry.chemical_classification ,Biological Products ,Molecular Structure ,010405 organic chemistry ,Aryl ,Organic Chemistry ,Total synthesis ,0104 chemical sciences ,Aglycone ,Xanthenes ,chemistry ,Alcohols ,Organic synthesis - Abstract
Hexacyclic xanthone natural products such as IB-00208 present a formidable challenge in organic synthesis. A new approach to polycyclic 1,4-dioxygenated xanthones from benzocyclobutenones has been developed and applied to the first total synthesis of the aglycone of IB-00208. The 22-step synthesis features an acetylide stitching process that joins an aryl aldehyde with an angularly fused benzocyclobutenone, which was prepared by a ring-closing metathesis reaction. The resulting acetylenic benzocyclobutenone diol underwent a Moore rearrangement to give an intermediate that was further elaborated to the aglycone of IB-00208 as a mixture of hydroquinone–quinone tautomers. more...
- Published
- 2014
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