Journal
ORGANIC LETTERS
Volume 13, Issue 21, Pages 5816-5819Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol2024289
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Funding
- Duke University
- NCBC [2008-IDG-1010]
- NSF [0923097]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0923097] Funding Source: National Science Foundation
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The total synthesis of psymberin was achieved employing a readily available chiral epoxide to prepare two of the three subunits in the natural product. The key reaction was a highly stereoselective organocatalytic oxa-conjugate addition reaction of alpha,beta-unsaturated ketone catalyzed by primary diamine for the synthesis of the 2,6-trans-tetrahydropyran embedded in psymberin.
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