Total Synthesis of (-)-Neocosmosin A via Intramolecular Diels-Alder Reaction of 2-Pyrone

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29
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SCOPUS

30

초록

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.

키워드

RESORCYLIC ACID LACTONESREGIOSELECTIVE SYNTHESIS3,5-DIBROMO-2-PYRONEBIOSYNTHESISCHEMISTRY(E)-BETA-BORYLSTYRENECYCLOADDITIONSMACROLACTONES(+/-)-CRININENEOCOSMOSIN
제목
Total Synthesis of (-)-Neocosmosin A via Intramolecular Diels-Alder Reaction of 2-Pyrone
저자
Lee, Joon-HoCho, Cheon-Gyu
DOI
10.1021/acs.orglett.6b02575
발행일
2016-10
유형
Article
저널명
Organic Letters
18
19
페이지
5126 ~ 5129