Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 20, Pages 7812-7821Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo901547k
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Funding
- EPSRC [GR/S77301/01]
- Higher Education Commission of Pakistan
- Merck Sharp and Dohme Ltd.
- University of Nottingham
- University of York
- University of York Department of Chemistry's Wild Fund
- Engineering and Physical Sciences Research Council [GR/S77301/01] Funding Source: researchfish
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A synthesis of the ABC-rings of the polyketide natural product hexacyclinic acid has been achieved. The B-ring was formed first via an intramolecular ester-tethered Diels-Alder reaction, and the A-ring was annulated to this by means of a SmI2 mediated reductive 5-exo-trig cyclization of a samarium-ketyl radical onto a vinyl group. Finally, the C-ring was closed using olefin metathesis. Interestingly, use of enyne metathesis resulted in the synthesis of a more functionalized 5-membered C-ring in a model system, but an undesired 6-membered C-ring in the actual system. An investigation of this change in selectivity is discussed.
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