Selim, Khalid B. Lee, Baeck Kyoung Sim, Taebo 2024-01-20T13:34:46Z 2024-01-20T13:34:46Z 2021-09-05 2012-10-31 0040-4039 https://pubs.kist.re.kr/handle/201004/128752 A synthesis of the E-isomer of the proposed structure of the novel tripeptide, lucentamycin A. was performed in an attempt to define the correct stereochemistry of this natural product. The synthetic route developed employs a stereoselective Rh-catalyzed reductive cyclization process to generate the key pyrrolidine residue in the target and a stereospecific inversion of the Z-olefin geometry to form desired E-isomer. Subsequent amide coupling reactions afforded the desired E-isomer of putative lucentamycin A. A comparison of the NMR data of synthetic E-la with that of the naturally occurring lucentamycin A demonstrated that they are not identical substances and the E-la was found to display no anti-proliferative activity on the colon cancer cell line HCT-116 in contrast to natural lucentamycin A. (C) 2012 Elsevier Ltd. All rights reserved. English PERGAMON-ELSEVIER SCIENCE LTD CATALYZED REDUCTIVE CYCLIZATION C BOND FORMATION ELECTROPHILIC ACTIVATION CYCLOISOMERIZATION 1,6-ENYNES HYDROGENATION 1,N-ENYNES EPOXIDES ENYNES ROUTE Stereoselective total synthesis of the E-isomer of putative lucentamycin A Article 10.1016/j.tetlet.2012.08.092 1 TETRAHEDRON LETTERS, v.53, no.44, pp.5895 - 5898 TETRAHEDRON LETTERS 53 44 5895 5898 scie scopus 000310170300020 2-s2.0-84866764718 Chemistry, Organic Chemistry Article CATALYZED REDUCTIVE CYCLIZATION C BOND FORMATION ELECTROPHILIC ACTIVATION CYCLOISOMERIZATION 1,6-ENYNES HYDROGENATION 1,N-ENYNES EPOXIDES ENYNES ROUTE E-Lucentamycin A Olefin geometry Reductive cyclization Natural product Chemical elucidation