Journal
ORGANIC LETTERS
Volume 13, Issue 19, Pages 5350-5353Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol202210k
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Funding
- Spanish Ministerio de Ciencia e Innovacion (MICINN)
- Fondos FEDER [CTQ2009-09692]
- Generalitat de Catalunya [2009SGR825]
- FPU, Ministerio de Educacion
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A substrate-controlled synthesis of (+)-herboxidiene from two lactate-derived chiral ketones is described. Remarkably, most of the carbon backbone was constructed through highly stereoselective titanium-mediated aldol reactions and an Ireland-Claisen rearrangement. Furthermore, an oxa-Michael cyclization and a high-yield Suzuki coupling were used to assemble the pyran ring and the diene moiety respectively.
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