Enantioselective Total Syntheses of (R)- and (S)-Naphthotectone, and Stereochemical Assignment of the Natural Product

被引：4

作者：

Guerrero-Vasquez, Guillermo A. ^{[1
]}

Galarza, Flavia A. D. ^{[2
]}

Molinillo, Jose M. G. ^{[1
]}

Andrade, Carlos Kleber Z. ^{[2
]}

Macias, Francisco A. ^{[1
]}

机构：

[1] Univ Cadiz, Allelopathy Grp, INBIO Inst Biomol, C Republ Saharaui S-N, Puerto Real 11510, Spain

[2] Univ Brasilia, Inst Quim, Lab Quim Metodol & Organ Sintet LaQMOS, CP 4478, BR-70910970 Brasilia, DF, Brazil

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 08期

关键词：

Total synthesis; Natural products; Fused ring systems; Quinones; Configuration determination; Electrochemistry; CONVENIENT SYNTHESIS; TECTONA-GRANDIS; NAPHTHOQUINONES; NAPHTHAZARIN; DERIVATIVES; CHEMISTRY; QUINONES; SHIKONIN; ALKANNIN; REAGENT;

D O I：

10.1002/ejoc.201501479

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both isomers of naphthotectone, an isoprenoid quinone from Verbenaceae Tectona grandis possessing interesting biological activities, were enantioselectively obtained by two different synthetic routes in which the carbon side-chain of the naphthoquinone core was introduced using either a Sonogashira or a Heck coupling reaction. In both cases, the naphthoquinone core of the final products was obtained by a late-stage anodic treatment. (R)-Naphthotectone was obtained in six steps from leuconaphthazarin with an overall yield of 38 % and an enantiomeric excess of 86 %. This compound was found to have the same absolute configuration as the natural product at its C-3' stereogenic center. (S)-Naphthotectone was obtained in five steps from leuconaphthazarin with an overall yield of 36 % and an enantiomeric excess of 80 %.

引用

页码：1599 / 1605

页数：7

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