Biomimetic Total Synthesis of Proto-Daphniphylline
Abstract
Proto-daphniphylline, the imputed biogenetic parent of the Daphniphyllum alkaloids, has been assembled in a biogenetically styled laboratory synthesis in which a pentacyclization process is the fundamental synthetic stratagem. This extraordinary transformation involves the formation of six σ-bonds under the influence of three elementary reagents-potassium hydroxide, ammonia, and acetic acid. The facility of the process adds credibility to the previous speculation that a similar process is an important step in the biosynthesis of the Daphniphyllum alkaloids.
- Publication:
-
Science
- Pub Date:
- June 1990
- DOI:
- 10.1126/science.248.4962.1532
- Bibcode:
- 1990Sci...248.1532P