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Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2018 Jan 19; Vol. 83 (2), pp. 980-992. Date of Electronic Publication: 2018 Jan 08. - Publication Year :
- 2018
-
Abstract
- A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (-)-aspinolide A and (-)-5-epi-aspinolide A utilizing a catalytic Nozaki-Hiyama-Kishi reaction to close the macrolide in the final step in 65-84% yields.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 83
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 29271194
- Full Text :
- https://doi.org/10.1021/acs.joc.7b02324