Biomimetic daphniphyllum alkaloids

It was of substantial interest when Heathcock and coworkers proposed a biogenetic pathway for daphniphyllum alkaloids [4,5] and demonstrated a biomimetic total synthesis of several of them. This review describes the recent studies on alkaloids isolated from the genus Daphniphyllum, the proposed biogenetic pathway, syntheses of daphniphyllum alkaloids based on these biogenetic proposals, and their activities. 

Section 18.2 surveys all the daphniphyllum alkaloids isolated so far, including our recent vork, while Sections 18.3-18.5 mainly deal with biogenetic pathways, total syntheses, the biomimetic synthesis, and the activities of these compounds. 

Codaphniphylline, one of the C30 daphniphyllum alkaloids, was synthesized by a modification of Heathcock s biomimetic approach [74], Modification was carried out by changing the tetrahydropyran to a tetrahydrofuran as in 189 (Scheme 18,27),... 

C. H. Heathcock, M. M. Hansen, R. B. Ruggeri, J. C. Kath, Daphniphyllum alkaloids.il. Biomimetic total synthesis of methyl homosecodaphniphyllate. Development of the tetracylization reaction, J. Org. Chem. 57 (1992) 2544-2553. 

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