A key improvement to the original saframycin B synthesis involves efficient sequential piperazinedione condensations to yield a basic saframycin skeleton from which all congeners might be made. Approaches toward the total synthesis of saframycin A result in formation of two advanced intermediates. The first, a pentacyclic diphenol nitrile with at least four out of five stereocenters established, is synthesized via a multistep scheme which involves a Pictet-Spengler type phenolic cyclization. The second advanced intermediate is produced via a route which involves cleavage of an imidazolidine ring with concomitant introduction of cyanide. An isomer of saframycin A is synthesized using this approach.
| Identifer | oai:union.ndltd.org:RICE/oai:scholarship.rice.edu:1911/16123 |
| Date | January 1988 |
| Creators | Ajeck-Carman, Karen Lynn |
| Contributors | Fukuyama, T. |
| Source Sets | Rice University |
| Language | English |
| Detected Language | English |
| Type | Thesis, Text |
| Format | 227 p., application/pdf |
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