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Total Syntheses of Disorazoles A₁ and B₁ and Full Structural Elucidation of Disorazole B₁.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2017 Nov 08; Vol. 139 (44), pp. 15636-15639. Date of Electronic Publication: 2017 Oct 24. - Publication Year :
- 2017
-
Abstract
- Described herein are the first total syntheses of naturally occurring antitumor agents disorazoles A <subscript>1</subscript> and B <subscript>1</subscript> and the full structural assignment of the latter. The syntheses were achieved through convergent strategies employing enantioselective constructions of the required building blocks, including a novel Sharpless epoxidation/enzymatic kinetic resolution of stannane-containing substrates that led selectively to both enantiomeric forms of an epoxy vinyl stannane, and a series of coupling reactions, including a Wittig reaction, a Suzuki coupling, a Stille coupling, a Yamaguchi esterification and a Yamaguchi macrolactonization.
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 139
- Issue :
- 44
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 29064682
- Full Text :
- https://doi.org/10.1021/jacs.7b09843