Stereoselective\nSynthesis of Spirolactone Analogues\nof Pyrrolomorpholine Alkaloids

The synthesis of a spirolactone analogue of xylapyrraside\nB<sub>1</sub>, a potent antioxidant agent, is described. The key step\nis\nthe stereoselective formation of the spirolactone skeleton via the\nformal [3+2] annulation of the isopropylidene-protected glyceraldehyde\nand δ-methylene lactone, mediated by trifluoroborane etherate.\nThis study addresses the stereoselective synthesis of pyrrolomorpholine\nspiroketal alkaloids, enabling the production of these bioactive compounds\nand their analogues.

Publication Details

Journal
Figshare
Published
2024-08-20
DOI
https://doi.org/10.1021/acs.joc.4c01608.s001
Primary Topic
Traditional and Medicinal Uses of Annonaceae
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article
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article

Stereoselective\nSynthesis of Spirolactone Analogues\nof Pyrrolomorpholine Alkaloids

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Traditional and Medicinal Uses of Annonaceae
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Stereoselective\nSynthesis of Spirolactone Analogues\nof Pyrrolomorpholine Alkaloids

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Abstract

The synthesis of a spirolactone analogue of xylapyrraside\nB<sub>1</sub>, a potent antioxidant agent, is described. The key step\nis\nthe stereoselective formation of the spirolactone skeleton via the\nformal [3+2] annulation of the isopropylidene-protected glyceraldehyde\nand δ-methylene lactone, mediated by trifluoroborane etherate.\nThis study addresses the stereoselective synthesis of pyrrolomorpholine\nspiroketal alkaloids, enabling the production of these bioactive compounds\nand their analogues.

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Traditional and Medicinal Uses of Annonaceae
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Stereoselective\nSynthesis of Spirolactone Analogues\nof Pyrrolomorpholine Alkaloids · Figshare (2024) | TGRS Research Map | TGRS