Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 8, Pages 3091-3102Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b13799
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Funding
- U.S. National Science Foundation [CHE1265964, CHE-1661612]
- U.S. National Institute of General Medical Sciences [R01GM098601, 1F31GM113494]
- NSF
- NIH
- National Science Foundation [CHE-1464828]
- Direct For Mathematical & Physical Scien [1464828] Funding Source: National Science Foundation
- Division Of Chemistry [1464828] Funding Source: National Science Foundation
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The first total synthesis of a chromodorolide marine diterpenoid is described. The core of the diterpenoid is constructed by a bimolecular radical addition/cyclization/fragmentation cascade that unites two complex fragments and forms two C-C bonds and four contiguous stereogenic centers of (-)-chromodorolide B in a single step. This coupling step is initiated by visible-light photocatalytic fragmentation of a redox-active ester, which can be accomplished in the presence of an iridium or a less-precious electron-rich dicyanobenzene photocatalyst, and employs equimolar amounts of the two addends. Computational studies guided the development of this central step of the synthesis and provide insight into the origin of the observed stereoselectivity.
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