Journal
ORGANIC LETTERS
Volume 14, Issue 21, Pages 5388-5391Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol302265z
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Funding
- NIH [R01GM071779, P41GM081282]
- NSF [CHE-1048804]
- Christian Bustillos
- National Key Technologies R&D Program of China [2012BAK25B03]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1048804] Funding Source: National Science Foundation
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A highly torquoselective thermal triene 6 pi electrocyclization controls the relative stereochemistry between the C3 and C18 stereocenters of the dodecahydroindolo[2,3-a]benzo[g]quinolizine skeleton of reserpine-type alkaloids. Employing a tandem cross-coupling/electrocyclization protocol allowed us to form the requisite triene and ensure its subsequent cyclization. A novel low-temperature dibromoketene acetal Claisen rearrangement established the requisite exocyclic dienylbromide precursor for the palladium-catalyzed cross-coupling reaction.
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