Intramolecular 1,8-diketone aldol reactions were studied as a tool for the construction of the seven-membered rings of hypocrellin and shiraiachrome. Conditions were identified to obtain the relative stereochemistries present in the two natural products with excellent diastereoselectivity. In addition, a nine-membered ring congener, which has yet to be observed in nature, formed with high selectivity when a hindered amine was used in conjunction with silazide bases.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2798919 | PMC |
| http://dx.doi.org/10.1021/jo9018914 | DOI Listing |
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