An efficacious, asymmetric synthesis of the 2, 9-dioxabicyclo [3, 3, 1] nonane 4 has been completed in nine chemical steps from 4, 5-dimethylfuraldehyde (8). Since enantiomerically pure 4 has been previously converted in five steps by Ireland into (+)-tirandamycic acid (3) and more recently by Schlessinger into (-)-tirandamycin A (1), this achievement constitutes in a strictly formal sense the total syntheses of these substances. The key step in the ...
