Ciufolini, Marco A.2009-06-042009-06-041998Chen, Mingying. "A new methodology for the total synthesis of mitomycinoid FR900482." (1998) Master’s Thesis, Rice University. <a href="https://hdl.handle.net/1911/17160">https://hdl.handle.net/1911/17160</a>.https://hdl.handle.net/1911/17160We describe the application of a novel ene-like reaction developed in our laboratory to the facile preparation of benzazocinone and benzazocenone intermediates of the type 3. Thus, ene-like reaction of 1 with 2-methoxypropene furnished adduct 2. This material underwent tandem intramolecular 1,3-dipolar azide cycloaddition and photolysis of the resulting triazoline to give 3. (DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE MAI) The newly developed avenue to these medium-ring heterocycles should be useful in a total synthesis of the antitumor agent, FR900482, 4. A synthesis of the highly substituted aldehyde 6, which could produce intermediates 5 suitable for the ultimate elaboration into 4 by the new chemistry, has also been developed.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE MAI)96 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 chemistryThesisTHESIS CHEM. 1998 CHEN