Ciufolini, Marco A.2009-06-042009-06-041998Zhu, Shuren. "Application of a novel carbonyl ene reaction: Total syntheses of phyllanthocin and chlorovulone II." (1998) Diss., Rice University. <a href="https://hdl.handle.net/1911/19334">https://hdl.handle.net/1911/19334</a>.https://hdl.handle.net/1911/19334We describe the total syntheses of $(\pm)$-phyllanthocin (1), the aglycon of the potent antineoplastic agent phyllanthoside (2a), and of $(\pm)$-chlorovulone II (3), a halogenated marine prostanoid with high antiproliferative and cytotoxic activity.* The key step of both syntheses is a novel carbonyl ene reaction, which occurs between ordinary aldehydes and vinyl ethers that display the oxygen functionality at the central carbon of an allylic system, e.g., 2-methoxypropene, under the catalytic influence of 0.5 mol% of the 1:1 complex of Yb(fod)$\sb3$ and acetic acid (Figure I).* ftn*Please refer to dissertation for diagrams.163 p.application/pdfengCopyright is held by the author, unless otherwise indicated. Permission to reuse, publish, or reproduce the work beyond the bounds of fair use or other exemptions to copyright law must be obtained from the copyright holder.Organic chemistryPharmaceutical sciencesThesisTHESIS CHEM. 1998 ZHU