We 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)
| Identifer | oai:union.ndltd.org:RICE/oai:scholarship.rice.edu:1911/17160 |
| Date | January 1998 |
| Creators | Chen, Mingying |
| Contributors | Ciufolini, M. A. |
| Source Sets | Rice University |
| Language | English |
| Detected Language | English |
| Type | Thesis, Text |
| Format | 96 p., application/pdf |
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