Journal
ORGANIC LETTERS
Volume 17, Issue 9, Pages 2118-2121Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b00707
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Funding
- Aix Marseille Universite
- CNRS
- COST ORCA Action [0905]
- French Research Ministry
- Agence Nationale de la Recherche (Orcademe Project) [ANR-10-JCJC-0710]
- Agence Nationale de la Recherche (ANR) [ANR-10-JCJC-0710] Funding Source: Agence Nationale de la Recherche (ANR)
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A general and highly efficient organocatalyzed desymmetrization of acyclic meso 1,3-diols through acyl transfer using chiral isothioureas is described. The introduction of p-systems in the acyclic substrates provided new opportunities in terms of reactivity, enantioselectivity and synthetic potential. To reach this high level of enantioselectivity (up to er >99:1), the reaction proceeds through a synergistic mechanism involving a desymmetrization reaction and a chiroablative kinetic resolution process. This methodology was used with success as the sole enantioselective catalytic step (developed on a gram scale) to achieve the total synthesis of the antiosteoporotic diarylheptanoid (-)-diospongin A (7 steps).
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