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Stereoselective Synthesis of Erythronolide A via Nitrile Oxide Cycloadditions and Related Studies
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Abstract
An expeditious synthesis of erythronolide A is documented. Key steps of the approach include two magnesium-mediated nitrile oxide cycloadditions, a chelation-controlled Grignard reaction, and a Sharpless asymmetric dihydroxylation.
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This article has been cited by 1 ACS Journal articles (1 most recent appear below).
Direct Entry to Erythronolides via a Cyclic Bis[Allene]
Kai Liu, Hiyun Kim, Partha Ghosh, Novruz G. Akhmedov, and Lawrence J. WilliamsJournal of the American Chemical Society2011 133 (38), 14968-14971Direct Entry to Erythronolides via a Cyclic Bis[Allene]
Kai Liu, Hiyun Kim, Partha Ghosh, Novruz G. Akhmedov, and Lawrence J. WilliamsJournal of the American Chemical Society2011 133 (38), 14968-14971The complexity and low tractability of antibiotic macrolides pose serious challenges to addressing the problem of resistance through semi- or total synthesis. Here we describe a new strategy involving the preparation of a complex yet tractable macrocycle ...
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History
- Published In Issue November 20, 2009
- Article ASAPOctober 19, 2009
- Received: August 23, 2009
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