Formal Synthesis of (−)-Haliclonin A: Stereoselective Construction of an Azabicyclo[3.3.1]nonane Ring System by a Tandem Radical Reaction
A formal synthesis of (−)-haliclonin A, isolated from the marine sponge Haliclona sp. in Korea, is described. The key feature of the synthesis includes the highly stereoselective tandem radical reaction to construct the azabicyclo[3.3.1]nonane core and the enantioselective formation of an all-carbo...
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| Published in | Organic letters Vol. 22; no. 13; pp. 5046 - 5050 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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American Chemical Society
02.07.2020
Amer Chemical Soc |
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| Abstract | A formal synthesis of (−)-haliclonin A, isolated from the marine sponge Haliclona sp. in Korea, is described. The key feature of the synthesis includes the highly stereoselective tandem radical reaction to construct the azabicyclo[3.3.1]nonane core and the enantioselective formation of an all-carbon quaternary center via the Pd-mediated deracemization. |
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| AbstractList | A formal synthesis of (−)-haliclonin A, isolated from the marine sponge Haliclona sp. in Korea, is described. The key feature of the synthesis includes the highly stereoselective tandem radical reaction to construct the azabicyclo[3.3.1]nonane core and the enantioselective formation of an all-carbon quaternary center via the Pd-mediated deracemization. A formal synthesis of (-)-haliclonin A, isolated from the marine sponge Haliclona sp. in Korea, is described. The key feature of the synthesis includes the highly stereoselective tandem radical reaction to construct the azabicyclo[3.3.1]nonane core and the enantioselective formation of an all-carbon quaternary center via the Pd-mediated deracemization. |
| Author | Hosaka, Taku Komine, Keita Fukuda, Hayato Ishihara, Jun Yamashita, Yuki Urayama, Yasuhiro Hatakeyama, Susumi |
| AuthorAffiliation | Medical Innovation Center Nagasaki University Graduate School of Biomedical Sciences |
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| Cites_doi | 10.1021/jacs.6b00541 10.1021/ol201758a 10.1021/ja026216d 10.1021/jacs.7b10177 10.1002/chir.23173 10.1002/chem.201203203 10.1016/j.tetlet.2004.05.133 10.1002/anie.201107370 10.1021/ol900282m 10.1021/ja311241q 10.1002/anie.201512005 10.1002/slct.201900396 10.1055/s-0037-1609150 10.1016/j.tet.2011.01.003 10.1126/science.aaf6742 10.1016/j.cclet.2017.04.016 10.3390/md17120682 10.1021/ol0400342 10.1002/chem.200802415 10.1021/ja0510616 10.1021/cr9601425 10.1039/p19940000369 10.1002/9783527615230 10.1021/ja00212a046 10.1021/jo00870a052 10.1016/S0040-4020(97)00781-3 10.1246/bcsj.57.1948 10.1016/S0040-4039(99)00286-5 |
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| Snippet | A formal synthesis of (−)-haliclonin A, isolated from the marine sponge Haliclona sp. in Korea, is described. The key feature of the synthesis includes the... A formal synthesis of (-)-haliclonin A, isolated from the marine sponge Haliclona sp. in Korea, is described. The key feature of the synthesis includes the... |
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| Title | Formal Synthesis of (−)-Haliclonin A: Stereoselective Construction of an Azabicyclo[3.3.1]nonane Ring System by a Tandem Radical Reaction |
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