Efficient synthesis of an A-B-C-tricycle fragment for a structural model of tolyporphin

Article abstract of DOI:10.1142/S1088424610001763

An efficient stereocontrolled synthesis of an A-B-C-tricycle fragment 7 for a structural model of tolyporphin 3 is described. All the rings were prepared from readily available starting materials. One of the two key steps is a selective ring-opening reaction of the lactone cycle in bicyclolactam-lactone 17 to cyanopyrrolidone 18, which introduces the chirality into synthetic compounds. The other key step is the combination of A ring with B-C-bicycle via a two-time Eschenmoser sulfide contraction. A-B-C-tricycle fragment 7 allows a new approach toward tolypophin compounds and other uroporphinoids.

Full text of DOI:10.1142/S1088424610001763

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