期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 42, 页码 17482-17485出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja308826x
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资金
- EPSRC
- GlaxoSmithKline
- Austrian Science Fund (FWF)
- EPSRC [EP/G007802/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/G007802/1] Funding Source: researchfish
Total syntheses of three structurally complex marine natural products, manzamine A, ircinol A, and ircinal A, are reported. The route pivoted on the construction of a late-stage protecting-group-free pentacyclic enol triflate coupling partner, from which all three family members were accessed divergently via palladium-catalyzed reactions. The rapid synthesis of this key pentacyclic enol triflate was achieved by a highly convergent union of five fragments through a stereoselective Michael addition, a three-component nitro-Mannich lactamization cascade, an unprecedented and highly stereoselective reductive nitro-Mannich cyclization cascade, a stereoselective organometallic addition, and a Z-selective alkene ring-closing metathesis. Altogether this chemistry has allowed the shortest synthetic route to date for manzamine A (18-step longest linear sequence) via a late-stage diversification point that is ideal for future manzamine A analogue synthesis.
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