Total Synthesis of the Aglycone of IB-00208.
A total synthesis of the aglycone of IB-00208 was accomplished in 22 steps using a newly developed approach towards polycyclic 1,4-dioxygenated xanthones from benzocyclobutenones. The generality of this entry to xanthones was initially established on several model systems before it was successfully applied to the construction of the hexacyclic core of the natural product. A new and potentially general approach towards angularly-fused benzocyclobutenones using ring-closing metathesis (RCM) was also developed.
Daniel
D
Knueppel
Department of Chemistry and Biochemistry and The Texas Institute for Drug and Diagnostic Development The University of Texas at Austin, 1 University Station A5300, Austin, TX 78712-0165.
Jingyue
J
Yang
Bo
B
Cheng
Douglas
D
Mans
Department of Chemistry and Biochemistry and The Texas Institute for Drug and Diagnostic Development The University of Texas at Austin, 1 University Station A5300, Austin, TX 78712-0165.
Stephen F
SF
Martin
Moore rearrangement; cyclobutenediones; natural products; polycyclic xanthones; total synthesis