Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C via Convergent Fragment Coupling Using a Tertiary Carbon Radical
SCIE
SCOPUS
- Title
- Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C via Convergent Fragment Coupling Using a Tertiary Carbon Radical
- Authors
- Garnsey, Michelle R.; Slutskyy, Yuriy; Jamison, Christopher R.; Zhao, Peng; Lee, Juyeol; Rhee, Young Ho; Oyerman, Larry E.
- Date Issued
- 2018-07
- Publisher
- AMER CHEMICAL SOC
- Abstract
- 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.
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/99270
- DOI
- 10.1021/acs.joc.7b02458
- ISSN
- 0022-3263
- Article Type
- Article
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, vol. 83, no. 13, page. 6958 - 6976, 2018-07
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- There are no files associated with this item.
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