期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 11, 页码 4522-4532出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo200418y
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资金
- Japan Society for the Promotion of Science (JSPS) [19590001, 21590001]
- Grants-in-Aid for Scientific Research [23310145, 19590001, 21590001] Funding Source: KAKEN
We successfully synthesized two enantiomers of bicyclic enones, (7R,7aR)- and (7S,7aS)-9, from the hemiacetal 2a, which we first synthesized from the symmetrical diketone la via diastereoselective carbon oxygen bond formation between one of the carbonyl groups and the chiral alcohol on the C2 side chain in a 2,2-disubstituted 1,3-cycloalkanedione derivative. We also report the total synthesis of natural (+)-lycopladine A [(+)-6] from (7R,7aR)-9 and the formal synthesis of unnatural (-)-lycopladine A [(-)-6] from (7S,7aS)-9.
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