Total Synthesis of the Marine Sponge Alkaloid Motuporamine C Using a Ramberg‐Bäcklund Ring Contraction Strategy. Issue 40 (25th October 2022)

• Record Type: Journal Article
• Authors: Song, Zijie; Meng, Shuyu; Wang, Quanrui
• Is Part Of: ChemistrySelect. Volume 7:Issue 40(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-10-25
• Subjects: alkene conversion -- macrocyclic amine -- macrocyclic thioetherification -- motuporamine C -- Ramberg-Bäcklund rearrangement; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202202991
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A new total synthesis of the marine alkaloid motuporamine C, a macrocyclic polyamine alkaloid from the marine sponge Xestospongia exigua, has been accomplished. Key steps of this synthesis include application of Ramberg‐Bäcklund rearrangement for achieving the 15‐membered aza‐macrocyclic alkene and Rh(II)‐catalyzed deoxygenation of epoxide for the conversion of E ‐ to Z ‐configuration of the double bond within the cyclic structure. Abstract : A new total synthesis to motuporamine C, the most abundant component of the related marine alkaloids, is accomplished starting from nonane‐1, 9‐diol and 5‐aminopentan‐1‐ol. The strategy relies on the application of stereoselective ring contraction by Ramberg‐Bäcklund reaction to achieve the 15‐membered aza‐olefin and Rh(II)‐catalyzed deoxygenation of epoxide for converting E ‐ to Z ‐configuration. All the required materials are easily and cheaply available, thus rendering this route appreciated.