Total Syntheses of Dihydroindole Aspidosperma Alkaloids: Reductive Interrupted Fischer Indolization Followed by Redox Diversification

被引：17

作者：

Martin, Gabor ^{[1
]}

Angyal, Peter ^{[1
]}

Egyed, Orsolya ^{[2
]}

Varga, Szilard ^{[1
]}

Soos, Tibor ^{[1
]}

机构：

[1] Res Ctr Nat Sci, Inst Organ Chem, H-1117 Budapest, Hungary

[2] Res Ctr Nat Sci, Instrumentat Ctr, H-1117 Budapest, Hungary

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 12期

关键词：

ENANTIOSELECTIVE TOTAL SYNTHESES; SECODINE INDOLE ALKALOIDS; MEERWEIN-PONNDORF-VERLEY; FORMAL SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; AKUAMMILINE ALKALOIDS; GENERAL ENTRY; (+)-ASPIDOSPERMIDINE; STRATEGY; (-)-ASPIDOSPERMIDINE;

D O I：

10.1021/acs.orglett.0c01472

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a novel reductive interrupted Fischer indolization process for the concise assembly of the 20-oxoaspidospermidine framework. This rapid complexity generating route paves the way toward various dihydroindole Aspidosperma alkaloids with different C-5 side chain redox patterns. The end-game redox modulations were accomplished by modified Wolff-Kishner reaction and photo-Wolff rearrangement, enabling the total synthesis of (-)-aspidospermidine, (-)-limaspermidine, and (+)-17-demethoxy-Nacetylcylindrocarine and the formal total synthesis of (-)-1-acetylaspidoalbidine.

引用

页码：4675 / 4679

页数：5

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