Journal
CHEMICAL COMMUNICATIONS
Volume 52, Issue 84, Pages 12426-12429Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cc06794h
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Funding
- National Science Foundation of China [21372016, 21572009, 21402002]
- Guangdong Natural Science Foundation [2014A030312004, 2016A030306011]
- NSFC-Shandong Joint Fund for Marine Science Research Centers [U1406402]
- Shenzhen Basic Research Program [ZDSYS20140509094114168, JSGG20140717102922014, JCYJ20150629144231017, JCYJ20160226105337556, JCYJ20160330095629781]
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Ozonolysis of aromatic abietane (+)-carnosic acid (4) is used to create an important intermediate in an enantiomerically pure form, resulting in a simple, concise, readily scalable, and asymmetric synthesis of (-)-antrocin (1). This strategy not only provides an efficient approach to (-)-antrocin (1) synthesis but can also be readily adopted for the syntheses of optically pure (+)-asperolide C (2) and (-)-trans-ozic acid (3) from the naturally abundant aromatic abietanes (+)-podocarpic acid (5) and (+)-dehydroabietic acid (6). The strategy presented here is an example of the use of naturally occurring aromatic abietanes as a chiral pool and offers an account of the asymmetric synthesis of terpenoids.
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