Bicyclomycin 1 is an antibiotic that is isolated from a culture filtrate of Streptomyces sapporonensis and Streptomyces aizunensis. Bicyclomycin exhibits a low toxicity and also possesses a unique chemical structure. Model studies of the synthesis are presented, however the total synthesis was not realized.
The critical reaction involves oxidative cyclization of a methylidenepiperazinedione to the bicyclo {4.4.2} system under basic conditions. This is then elaborated to include the carbon framework of the side chain. The two amides are protected throughout the model synthesis and possible protecting groups are described for an eventual total synthesis of bicyclomycin.
| Identifer | oai:union.ndltd.org:RICE/oai:scholarship.rice.edu:1911/15857 |
| Date | January 1984 |
| Creators | ROBINS, BARRY DOUGLAS |
| Source Sets | Rice University |
| Language | English |
| Detected Language | English |
| Type | Thesis, Text |
| Format | application/pdf |
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