title: Asymmetric Total Synthesis of Distaminolyne A and Revision of Its Absolute Configuration.
abstract: The first total synthesis of a marine derived polyacetylene, distaminolyne A, and its enantiomer were achieved from the commercially available undec-10-en-1-ol. A key proline-catalyzed asymmetric α-aminooxylation of an aldehyde intermediate was used to introduce the chiral center en route to the enantiomerically pure 1,2-amino alcohols. The absolute configuration of both synthesized enantiomers of distaminolyne A was confirmed by using chiral derivatizing agents, leading to revision of the natural product absolute configuration from 2S to 2R. Antibacterial, pancreatic lipase (PL) inhibitory, and protein-tyrosine phosphatase 1B (PTP1B) inhibitory activities were evaluated.
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , No. 555, Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.|School of Pharmaceutical Sciences, Jinzhou Medical University , Jinzhou 121001, China.
authors.forename: Dong-Yu
authors.initials: DY
authors.lastname: Sun
authors.affiliation: The First Affiliated Hospital of Jinzhou Medical University , No. 2, Renmin Road, Jinzhou 121001, China.
authors.forename: Guan-Ying
authors.initials: GY
authors.lastname: Han
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , No. 555, Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.
authors.forename: Jing-Xu
authors.initials: JX
authors.lastname: Gong
authors.affiliation: Laboratoire de Synthèse Organique (UMR 7652 CNRS), Ecole Polytechnique, Université Paris-Saclay , 91128 Palaiseau Cedex, France.
authors.forename: Bastien
authors.initials: B
authors.lastname: Nay
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , No. 555, Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.
authors.forename: Xu-Wen
authors.initials: XW
authors.lastname: Li
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , No. 555, Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.
authors.forename: Yue-Wei
authors.identifier: 0000-0003-0413-2070
authors.initials: YW
authors.lastname: Guo