Collective Asymmetric Total Syntheses of Marine Decahydroquinoline Alkaloid Lepadins A–E, H, and ent-I

Lepadins are cis-fused decahydroquinoline (DHQ) marine alkaloids that have shown diverse biological activities and have attracted extensive synthetic interest. A new collective synthetic strategy is reported that features a green chemistry approach for constructing the common cis-fused DHQ core, whi...

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Veröffentlicht in:Organic letters 2021-08, Vol.23 (16), p.6583-6588
Hauptverfasser: Ma, Foqing, He, Chenxi, Wang, Eryu, Tong, Rongbiao
Format: Artikel
Sprache:eng
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Zusammenfassung:Lepadins are cis-fused decahydroquinoline (DHQ) marine alkaloids that have shown diverse biological activities and have attracted extensive synthetic interest. A new collective synthetic strategy is reported that features a green chemistry approach for constructing the common cis-fused DHQ core, which is achieved through green oxone-halide oxidation for both the aza-Achmatowicz rearrangement and the intramolecular [3 + 2] cycloaddition of nitrile oxide–alkene. Collective total syntheses of lepadins A–E and H are accomplished from the common DHQ core within 10 steps.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02435