Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 40, Pages 13989-13992Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b07388
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Funding
- National Science Foundation of China [21632002, 21572009, 21402002]
- Guangdong Natural Science Foundation [2014A030312004, 2016A030306011]
- Shenzhen Basic Research Program [JCYJ20150629144231017, JCYJ20160226105337556]
- Qingdao National Laboratory for Marine Science and Technology [2015ASKJ02]
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The enantioselective synthesis of (-)-pavidolide B (1) was achieved in a linear sequence of 10 steps. The key steps are (a) an enantioselective organocatalytic cyclopropanation; (b) a radical-based cascade annulation for the regio- and diastereo-selective synthesis of the highly functionalized lactone 3 bearing the characteristic tricyclic core and seven contiguous stereocenters; (c) a sequential ring-closing metathesis reaction and a RhCl3-catalyzed double bond isomerization to form the seven-membered D ring of (-)-pavidolide B.
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