Ham, Young Jin Yu, Hana Kim, Nam Doo Hah, Jung-Mi Selim, Khalid B. Choi, Hwan Geun Sim, Taebo 2024-01-20T15:31:08Z 2024-01-20T15:31:08Z 2022-01-10 2012-02-18 0040-4020 https://pubs.kist.re.kr/handle/201004/129535 A Rh-catalyzed diastereoselective reductive cyclization, mediated by hydrogen, of optically active 1,6-enynes using chiral BINAP was successfully applied to the total synthesis of four stereoisomers of the proposed structure of lucentamycin A. In order to synthesize two of these four stereoisomers, we successfully constructed chiral proline derivatives bearing cis-carbon substituents at C2 and C3 positions based on Krische's methodology, which has very rarely been reported. Anti-proliferative activities on HCT-116 cell line and NMR data of these four stereoisomers were compared with those of naturally occurring lucentamycine A. The results show that the proposed structure of lucentamycin A needs revision. (C) 2012 Elsevier Ltd. All rights reserved. English PERGAMON-ELSEVIER SCIENCE LTD C BOND FORMATION ELECTROPHILIC ACTIVATION MECHANISTIC ASPECTS ENYNES CYCLOISOMERIZATION HYDROGEN METAL 1,N-ENYNES COMPLEXES DIYNES Rhodium-catalyzed reductive cyclization of 1,6-enynes and stereoselective synthesis of the putative structure of lucentamycin A and its stereoisomers Article 10.1016/j.tet.2011.12.075 1 TETRAHEDRON, v.68, no.7, pp.1918 - 1925 TETRAHEDRON 68 7 1918 1925 scie scopus 000300804400009 2-s2.0-84856402549 Chemistry, Organic Chemistry Article C BOND FORMATION ELECTROPHILIC ACTIVATION MECHANISTIC ASPECTS ENYNES CYCLOISOMERIZATION HYDROGEN METAL 1,N-ENYNES COMPLEXES DIYNES Lucentamycin A Structure revision 1,6-Enynes Reductive cyclization Natural product