Regioselective synthesis of the bridged tricyclic core of Garcinia natural products via intramolecular aryl acrylate cycloadditions.
[reaction: see text] Two different routes to the tricyclic core of Garcinia-derived natural products are described. The first approach is based on a tandem Claisen/Diels-Alder rearrangement and delivers the desired lactone 14. The second approach, employing a Wessely oxidation/Diels-Alder protocol, leads to the same caged heterocycle, albeit with modified constitution.
Tisdale
Eric J
EJ
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
Chowdhury
Chinmay
C
Vong
Binh G
BG
Li
Hongmei
H
Theodorakis
Emmanuel A
EA
D000179:Acrylates / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D029760:Garcinia / Q000737:chemistry*; D010084:Oxidation-Reduction
D000179:Acrylates; D001688:Biological Products; C036658:acrylic acid