Total\nSyntheses of Scabrolide B, Ineleganolide, and\nRelated Norcembranoids

Concise total syntheses of several\n5/7/6 norcembranoids, including\nineleganolide, scabrolide B, sinuscalide C, and fragilolide A have\nbeen achieved through a fragment coupling/ring closure approach. The\ncentral seven-membered ring was forged through sequential Mukaiyama–Michael/aldol\nreactions using norcarvone and a decorated bicyclic lactone incorporating\na latent electrophile. Subsequent manipulations installed the reactive\nenedione motif and delivered scabrolide B in 11 steps from a chiral\npool-derived enone. Finally, ineleganolide, sinuscalide C, and fragilolide\nA were each accessed in one additional step.

Publication Details

Journal
Figshare
Published
2024-12-20
DOI
https://doi.org/10.1021/jacs.4c16629.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
Field-Weighted Citation Impact
0.00
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article

Total\nSyntheses of Scabrolide B, Ineleganolide, and\nRelated Norcembranoids

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Mycorrhizal Fungi and Plant Interactions
article

Total\nSyntheses of Scabrolide B, Ineleganolide, and\nRelated Norcembranoids

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Abstract

Concise total syntheses of several\n5/7/6 norcembranoids, including\nineleganolide, scabrolide B, sinuscalide C, and fragilolide A have\nbeen achieved through a fragment coupling/ring closure approach. The\ncentral seven-membered ring was forged through sequential Mukaiyama–Michael/aldol\nreactions using norcarvone and a decorated bicyclic lactone incorporating\na latent electrophile. Subsequent manipulations installed the reactive\nenedione motif and delivered scabrolide B in 11 steps from a chiral\npool-derived enone. Finally, ineleganolide, sinuscalide C, and fragilolide\nA were each accessed in one additional step.

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Mycorrhizal Fungi and Plant Interactions
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