Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 3, Pages 418-419Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja109516f
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology of Japan [20002004, 22590002]
- Grants-in-Aid for Scientific Research [20002004, 22590002] Funding Source: KAKEN
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The total synthesis of lyconadin A from (R)-5-methylcyclohex-2-enone was accomplished. Our synthesis features the facile construction of a highly fused tetracyclic compound through a combination of an aza-Prins reaction and an electrocyclic ring opening. Transformation of the bromoalkene moiety in the tetracycle could be achieved by either a vinylogous Pummerer rearrangement or the formation and subsequent isomerization of the nitrosoalkene to furnish an alpha,beta-unsaturated ketone, from which the pyridone ring was constructed.
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