Kim, Byungsook Lee, Miseon Kim, Mi Jung Lee, Hyunjoo Kim, Sanghee Kim, Deukjoon Koh, Minseob Park, Seung Bum Shin, Kye Jung 2024-01-20T22:04:56Z 2024-01-20T22:04:56Z 2021-09-03 2008-12-10 0002-7863 https://pubs.kist.re.kr/handle/201004/132882 The first asymmetric total synthesis of (-)-laurefucin (1), a unique C-15 acetogenin with a 2,8-dioxabicyclo[5.2.1]decane skeleton, has been accomplished in nine steps in 31% overall yield from known oxocene 10. Highlights of the highly stereoselective synthesis include a novel organoselenium-mediated biomimetic hydroxyetherification. English AMER CHEMICAL SOC MEDIUM RING ETHERS LAURENCIA-PINNATIFIDA CARBONYL-COMPOUNDS C-15 ACETOGENINS (+)-LAURENCIN METABOLITES ABSOLUTE CONFIGURATION CONSTRUCTION CYCLIZATIONS Biomimetic Asymmetric Total Synthesis of (-)-Laurefucin via an Organoselenium-Mediated Intramolecular Hydroxyetherification Article 10.1021/ja806304s 1 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.130, no.49, pp.16807 - 16811 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 130 49 16807 16811 scie scopus 000263320200071 2-s2.0-57549083399 Chemistry, Multidisciplinary Chemistry Article MEDIUM RING ETHERS LAURENCIA-PINNATIFIDA CARBONYL-COMPOUNDS C-15 ACETOGENINS (+)-LAURENCIN METABOLITES ABSOLUTE CONFIGURATION CONSTRUCTION CYCLIZATIONS