Total Synthesis of the Marine Sponge Alkaloid Motuporamine C Using a Ramberg‐Bäcklund Ring Contraction Strategy

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...

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Bibliographic Details
Published inChemistrySelect (Weinheim) Vol. 7; no. 40
Main Authors Song, Zijie, Meng, Shuyu, Wang, Quanrui
Format Journal Article
LanguageEnglish
Published 26.10.2022
Subjects
alkene conversion
macrocyclic amine
macrocyclic thioetherification
motuporamine C
Ramberg-Bäcklund rearrangement
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Summary: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. 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.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202202991