SOME APPROACHES TO TOTAL SYNTHESIS OF LYCORINE

The problem of the synthesis of the lycorine family of Amaryllidaceae alkaloids is analyzed and two separate kinds of synthetic routes are examined experimentally. The first route, based on a Diels-Alder formation of ring C, leads to a product containing the lycorine skeleton with a nonaromatic ring C reasonably functionalized to complete the synthesis. The second approach, involving several variations on a roughly biosynthetic analogy, was frustrated on each occasion by reactions, usually internal conjugate additions, which took an undesirable course. © 1969, American Chemical Society. All rights reserved.