期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 13, 页码 6958-6976出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02458
关键词
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资金
- NSF [CHE1265964]
- National Research Foundation of Korea [NRF-2015R1A2A1A15056116]
- NSF
- NIH
- [1F31GM113494]
The development of a convergent fragment coupling strategy for the enantioselective total syntheses of a group of rearranged spongian diterpenoids that harbor the cis-2,8-dioxabicyclo[3.3.0]octan-3-one unit is described. The key bond disconnection relies on a late-stage fragment coupling between a tertiary carbon radical and an electron-deficient alkene to unite two ring systems and form two new stereocenters, one of which is quaternary, in a stereoselective and efficient manner. This strategy is applied toward scalable 14-15 step syntheses of three rearranged spongian diterpenoids, cheloviolenes A and B, and dendrillolide C.
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