Biomimetic Total Synthesis of Proto-Daphniphylline

Science  22 Jun 1990:
Vol. 248, Issue 4962, pp. 1532-1534
DOI: 10.1126/science.248.4962.1532


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 (r-bonds under the influence of three elementary reagents—potassium hydroxide, anmnonia, 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.