Stereoselective Synthesis of Spirolactone Analogues of Pyrrolomorpholine Alkaloids

The synthesis of a spirolactone analogue of xylapyrraside B1, a potent antioxidant agent, is described. The key step is the stereoselective formation of the spirolactone skeleton via the formal [3+2] annulation of the isopropylidene-protected glyceraldehyde and δ-methylene lactone, mediated by trifl...

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Published inJournal of organic chemistry Vol. 89; no. 17; pp. 12864 - 12870
Main Authors Uchiyama, Ami, Ohta, Hikari, Ogawa, Yuya, Sasaki, Ikuo, Sugimura, Hideyuki
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 06.09.2024
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Summary:The synthesis of a spirolactone analogue of xylapyrraside B1, a potent antioxidant agent, is described. The key step is the stereoselective formation of the spirolactone skeleton via the formal [3+2] annulation of the isopropylidene-protected glyceraldehyde and δ-methylene lactone, mediated by trifluoroborane etherate. This study addresses the stereoselective synthesis of pyrrolomorpholine spiroketal alkaloids, enabling the production of these bioactive compounds and their analogues.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01608