Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 24, Pages 15958-15971Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02230
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Funding
- National Science Foundation of China [21632002, 21572009, U1606403]
- Guangdong Natural Science Foundation [2016A030306011]
- Shenzhen Basic Research Program [JCYJ20170818090044432, JCYJ20160226105337556, GRCK2017042414425972]
- Qingdao National Laboratory for Marine Science and Technology [2015ASKJ02, LMDBKF201703]
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The development of an efficient strategy for the asymmetric total synthesis of the bioactive marine natural product (-)-pavidolide B is described in detail. The development process and detours leading to the key thiyl-radical-mediated [3 + 2] annulation reaction, which constructed the central C ring with four contiguous stereogenic centers in one step, are depicted. Subsequently, the seven -membered D ring is constructed via a ring-closing metathesis reaction followed by a Rh(III)-catalyzed isomerization. This strategy enables the total synthesis of (-)-pavidolide B in the longest linear sequence of 10 steps.
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