A novel synthetic route via iterative condensations of piperazinedione and substituted benzaldehydes has resulted in the first total synthesis of the complex antibiotic, renieramycin A 1a. Salient features include an acyliminium ion-mediated construction of a diazabicyclo (3.3.1) nonane nucleus, which allows for stereoselective hydrogenation and benzylic oxidation. The stereochemistry of the angelate side chain was unequivocally determined by X-ray crystallographic analysis of the penultimate intermediate, 67b. (DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI)
| Identifer | oai:union.ndltd.org:RICE/oai:scholarship.rice.edu:1911/16531 |
| Date | January 1992 |
| Creators | Linton, Steven Douglas |
| Contributors | Fukuyama, Tohru |
| Source Sets | Rice University |
| Language | English |
| Detected Language | English |
| Type | Thesis, Text |
| Format | 149 p., application/pdf |
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