Total synthesis of zoanthamine alkaloids

Accounts of Chemical Research
Fumihiko YoshimuraMasaaki Miyashita

Abstract

Zoanthamine alkaloids, isolated from organisms in the Zoanthus genus, constitute a distinctive family of marine metabolites. These molecules exhibit a broad spectrum of unique biological properties. For example, norzoanthamine inhibits interleukin-6, the key mediator of bone resorption in osteoporosis, providing a promising drug candidate for a disease that affects more than 10 million people over age 50 in the United States. In addition, these natural products are characterized by a densely functionalized heptacyclic framework, as exemplified by the structures of zoanthamine, norzoanthamine, and zoanthenol, which makes them extremely attractive targets for chemical synthesis. Prior to our first total synthesis of norzoanthamine in 2004, the densely functionalized and complex stereostructures of the zoanthamine alkaloids had impeded synthetic studies of these molecules. In this Account, we describe our synthetic approach toward the total synthesis of zoanthamine alkaloids, focusing on how we overcame various synthetic challenges. At the beginning of our synthetic studies, we aimed to develop an efficient route that was flexible enough to provide access to several members of the family while allowing the synthesis of various ana...Continue Reading

References

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Citations

Oct 16, 2014·Marine Drugs·Francisco Cen-PachecoAntonio Hernández Daranas
May 7, 2013·Natural Product Reports·Zhong Jin
Jan 17, 2017·European Journal of Organic Chemistry·Jeffrey T BagdanoffBrian M Stoltz
Feb 17, 2021·Bioscience, Biotechnology, and Biochemistry·Yoshimichi SakakibaraKengo Shigetomi
Apr 7, 2021·Angewandte Chemie·Zhengyuan XinShuanhu Gao
May 17, 2014·Organic Letters·Francisco Cen-PachecoAntonio Hernández Daranas

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