Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 9, Pages 3818-3837Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00489
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Funding
- Pfizer
- EPSRC [EP/K503150/1, EP/K039466/1]
- European Community [4494/4196]
- University of Southampton
- Engineering and Physical Sciences Research Council [EP/K039466/1] Funding Source: researchfish
- EPSRC [EP/K039466/1] Funding Source: UKRI
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A second-generation synthesis of (-)-luminacin D based on an early stage introduction of the trisubstituted epoxide group is reported, allowing access to the natural product in an improved yield and a reduced number of steps (5.4%, 17 steps vs 2.6%, 19 steps). A full account of the optimization work is provided, with the reversal of stereoselection in the formation of the C4 alcohol in equally excellent diastereoselectivity as the key improvement.
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