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Science 22 June 1990:
Vol. 248. no. 4962, pp. 1532 - 1534
DOI: 10.1126/science.248.4962.1532
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Articles

Biomimetic Total Synthesis of Proto-Daphniphylline

Serge Piettre 1 and Clayton H. Heathcock 1

1 Department of Chemistry, University of California, Berkeley, CA 94720

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.


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