Asymmetric, stereocontrolled total synthesis of (-)-brevianamide B
The asymmetric, stereocontrolled total synthesis of (-)-brevianamide B (2) is described. The synthesis features a stereocontrolled intramolecular S sub(N)2' cyclization to construct the central bicyclo(2.2.2) nucleus. A synthetic route to C-10-epibrevianamide A is also described. A synthetic sa...
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| Published in: | Journal of the American Chemical Society Vol. 112; no. 2; pp. 808 - 821 |
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| Main Authors: | , , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Washington, DC
American Chemical Society
1990
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| Abstract | The asymmetric, stereocontrolled total synthesis of (-)-brevianamide B (2) is described. The synthesis features a stereocontrolled intramolecular S sub(N)2' cyclization to construct the central bicyclo(2.2.2) nucleus. A synthetic route to C-10-epibrevianamide A is also described. A synthetic sample of a shunt metabolite proposed by Birch in 1972 has been prepared and its oxidation chemistry in the context of the proposed biosynthetic schemes is discussed. |
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| AbstractList | The asymmetric, stereocontrolled total synthesis of (-)-brevianamide B (2) is described. The synthesis features a stereocontrolled intramolecular S sub(N)2' cyclization to construct the central bicyclo(2.2.2) nucleus. A synthetic route to C-10-epibrevianamide A is also described. A synthetic sample of a shunt metabolite proposed by Birch in 1972 has been prepared and its oxidation chemistry in the context of the proposed biosynthetic schemes is discussed. |
| Author | Williams, Robert M Stille, James K Kwast, Ewa Glinka, Tomasz Coffman, Hazel |
| Author_xml | – sequence: 1 givenname: Robert M surname: Williams fullname: Williams, Robert M – sequence: 2 givenname: Tomasz surname: Glinka fullname: Glinka, Tomasz – sequence: 3 givenname: Ewa surname: Kwast fullname: Kwast, Ewa – sequence: 4 givenname: Hazel surname: Coffman fullname: Coffman, Hazel – sequence: 5 givenname: James K surname: Stille fullname: Stille, James K |
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| Keywords | Intramolecular reaction Angular nitrogen heterocycle Nitrogen heterocycle Lactam Tetracyclic compound Spiran Total synthesis Cyclization Asymmetric reaction Bicyclic compound SN2' mechanism Aromatic compound Enantiomer(-) |
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| Snippet | The asymmetric, stereocontrolled total synthesis of (-)-brevianamide B (2) is described. The synthesis features a stereocontrolled intramolecular S sub(N)2'... |
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| SubjectTerms | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry Preparations and properties |
| Title | Asymmetric, stereocontrolled total synthesis of (-)-brevianamide B |
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