Divergent Total Syntheses to Azafluoranthene and Dehydroaporphine Alkaloids

被引：15

作者：

Khunnawutmanotham, Nisachon ^{[1
]}

Sahakitpichan, Poolsak ^{[2
]}

Chimnoi, Nitirat ^{[2
]}

Techasakul, Supanna ^{[1
,3
,4
]}

机构：

[1] Chulabhorn Res Inst, Organ Synth Lab, Bangkok 10210, Thailand

[2] Chulabhorn Res Inst, Lab Nat Prod, Bangkok 10210, Thailand

[3] Kasetsart Univ, Dept Chem, Bangkok 10900, Thailand

[4] Kasetsart Univ, Fac Sci, Ctr Excellence Innovat Chem, Bangkok 10900, Thailand

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 28期

关键词：

Alkaloids; Synthetic methods; Natural products; Divergent synthesis; Polycycles; Domino reactions; CYCLIZATION; ARYLATION; RUFESCINE;

D O I：

10.1002/ejoc.201500866

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Facile divergent total syntheses for azafluoranthene and dehydroaporphine alkaloids have been successfully developed. A common intermediate, a biarylsulfonamide-protected amino aldehyde, underwent either a cascade or a stepwise cyclization to furnish a tetracyclic skeleton related to the azafluoranthene alkaloids. Natural products, triclisine and telitoxine, were prepared to illustrate the use of this approach. Subsequent C-homologation of the aldehyde moiety on the same intermediate by means of a Wittig reaction allowed the synthesis of aporphine alkaloids, as exemplified by the preparation of dehydronornuciferine. This synthetic approach could be applicable to the syntheses of other azafluoranthene-related as well as aporphine-related alkaloids.

引用

页码：6324 / 6332

页数：9

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