期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 3, 页码 1735-1745出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo5026699
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资金
- MEXT [2105, 25293003]
- Waseda University
The formal enantioselective total synthesis of nemorosone, garsubellin A, clusianone, and hyperforin is described. The catalytic asymmetric intramolecular cyclopropanation (CAIMCP) of an a-diazo ketone, a common synthetic intermediate for the above four polycyclic polyprenylated acylphloroglucinols previously reported by us, exhibited low enantioselectivity. However, CAIMCP of the corresponding alpha-diazo beta-keto sulfone afforded the desired product in 79% yield with 84% ee. Investigation of the CAIMCP of the alpha-diazo beta-keto sulfone demonstrated the formation of a rearrangement product in the presence of molecular sieves 4 angstrom, whereas, in the presence of H2O, the byproduct derived from ring-opening of the desired cyclopropane was observed. X-ray crystallographic analysis suggested that the above two products are derived from the same chiral intermediate. The product derived from ring-opening of the cyclopropane was successfully transformed to the respective synthetic intermediates for the total syntheses of nemorosone, garsubellin A, clusianone, and hyperforin, which had previously been reported by us.
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