Total synthesis of the novel, biologically active epoxyquinone dimer (+/-)-torreyanic acid: a biomimetic approach.
[reaction: see text] A total synthesis of the complex, biologically active, dimeric natural product (+/-)-torreyanic acid, which is composed of seven rings and laced with dense, variegated oxy-functionalization, has been accomplished from readily available allyl-substituted p-benzoquinone 8. Our synthetic stratagem involves crafting an epoxyquinone monomer for use in a biomimetic cascade process involving tandem a 6pi electrocyclization and a Diels-Alder dimerization.
Mehta
Goverdhan
G
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India. gm@orgchem.iisc.ernet.in
Pan
Subhas Chandra
SC