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Syntheses of Cyclopropyl Analogues of Disorazoles A 1 and B 1 and Their Thiazole Counterparts.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2018 Oct 19; Vol. 83 (20), pp. 12374-12389. Date of Electronic Publication: 2018 Oct 02. - Publication Year :
- 2018
-
Abstract
- Modular syntheses of disorazoles A <subscript>1</subscript> and B <subscript>1</subscript> analogues in which the epoxide moieties of the natural products were replaced with cyclopropyl units have been achieved. Targeted as part of a structure-activity relationships study, these syntheses were successfully extended to the thiazole counterparts of these analogues. The retrosynthetically defined fragments were assembled through Yamaguchi esterification, Cu/Pd-catalyzed cross-coupling, Yamaguchi macrolactonization, and Cu-catalyzed cross-coupling as the key reactions. Further synthetic and biological investigations of such analogues are expected to lead to the discovery and development of potential payloads for antibody-drug conjugates as targeted cancer therapies.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 83
- Issue :
- 20
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 30277774
- Full Text :
- https://doi.org/10.1021/acs.joc.8b02137