Complementary Asymmetric Routes to (R)-2-(7-Hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate
Organic Letters2012Vol. 14(24), pp. 6306–6309
Citations Over TimeTop 20% of 2012 papers
Thomas O. Schrader, Benjamin Johnson, Luis Lopez, Michelle Kasem, Tawfik Gharbaoui, Dipanjan Sengupta, Daniel J. Buzard, Christine Basmadjian, Robert M. Jones
Abstract
Two distinct and scalable enantioselective approaches to the tricyclic indole (R)-2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate, an important synthon for a preclinical S1P(1) receptor agonist, are reported. Route 1 employs a modified version of Smith's modular 2-substituted indole synthesis as the key transformation. Route 2 involves a highly enantioselective CuH-catalyzed 1,4-hydrosilylation as the stereodefining step. Both routes can be performed without chromatography to provide multigram quantities of the tricycle in ≥98% ee.
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