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- W1558914802 abstract "Publisher Summary This chapter discusses the total syntheses of zoapatanol by Nicolaou's synthesis, Chen's synthesis, Cookson's synthesis, Kocienski's synthesis, Kane's synthesis, Trost's synthesis, and by ring-closing metathesis approach and Homer-Wadsworth-Emmons approach. (+)-Zoapatanol, montanol, tomentanol, and tomentol are diterpenoid oxepanes isolated from the leaves of the Mexican zoapatle plant, Montanoa tomentosa , which Mexican women have been using for centuries to prepare tea to induce menses, labor, and terminate early pregnancy. Recent studies support the belief that zoapatanol and its metabolites might be responsible for the observed antifertility activity. Due to its biological profile and its challenging structure, several synthetic approaches have been described and seven total syntheses of zoapatanol have been reported, but only two of them were enantioselective. Key issues for a successful synthesis of zoapatanol are the stereocontrolled construction of the oxepane ring containing the two stereogenic centers, the introduction of the (E)-exocyclic double bond and the installation of the nonenyl side chain. Since (+)-zoapatanol was isolated as a 1/1 mixture of epimers at C6, control of this stereocenter is not required. The first two syntheses of (+)-zoapatanol were, one by Nicolaou and the other by Chen and Rowand, and six other syntheses have been disclosed since then. For all of them, the construction of the oxepane ring was achieved through the formation of the O1′-C7′ or O1′-C2′ bonds except for one in which the C4′-C5′ bond was formed." @default.
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- W1558914802 date "2008-01-01" @default.
- W1558914802 modified "2023-09-24" @default.
- W1558914802 title "Chapter 3 Total syntheses of zoapatanol" @default.
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- W1558914802 doi "https://doi.org/10.1016/s1874-6004(08)80007-x" @default.
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