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Total Synthesis of (-)-Neocosmosin A via Intramolecular Diels-Alder Reaction of 2-Pyrone
- Authors
- Lee, Joon-Ho; Cho, Cheon-Gyu
- Issue Date
- Oct-2016
- Publisher
- AMER CHEMICAL SOC
- Citation
- ORGANIC LETTERS, v.18, no.19, pp.5126 - 5129
- Indexed
- SCIE
SCOPUS
- Journal Title
- ORGANIC LETTERS
- Volume
- 18
- Number
- 19
- Start Page
- 5126
- End Page
- 5129
- ISSN
- 1523-7060
- Abstract
- A new synthetic route to (-)-neocosmosin A was devised by elaboration, of intramolecular Diels- Alder (IMDA) cycloaddition of 2-pyrone containing a bromopropiolate group as the dienophile. The IMDA reaction was accompanied by cycloreversion of carbon dioxide to give benzannulated macrolide with two bromide groups at C14 and C16. Installation of the pinacolboryl groups and oxidations allowed completion of the total synthesis of (-)-neocosmosin A.
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Related Researcher
- Cho, Cheon Gyu
- COLLEGE OF NATURAL SCIENCES (DEPARTMENT OF CHEMISTRY)