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Design and synthesis of a hybrid framework of indanone and chromane: total synthesis of a homoisoflavanoid, brazilane

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Abstract

A chemical backbone of tetracyclic homoisoflavanoid natural products such as brazilin inspired us to design a new chemical scaffold, 6a,11b-dihydroindeno[2,1-c]chromen-7(6H)-one, which is a hybrid structure of indanone and chromane. Pd-catalyzed Suzuki–Miyaura cross-coupling of 4-chloro-2H-chromene-3-carbaldehydes with (hetero)aryl boronic acids was employed as a means to introduce a wide variety of (hetero)aryl groups as the D ring and intramolecular Friedel–Crafts acylation was utilized to construct the C ring of this skeleton. Total synthesis of the natural product, brazilane, was also demonstrated via this new chemical framework.

Graphical abstract: Design and synthesis of a hybrid framework of indanone and chromane: total synthesis of a homoisoflavanoid, brazilane

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Publication details

The article was received on 10 Nov 2017, accepted on 27 Nov 2017 and first published on 27 Nov 2017


Article type: Paper
DOI: 10.1039/C7OB02758C
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Design and synthesis of a hybrid framework of indanone and chromane: total synthesis of a homoisoflavanoid, brazilane

    J. Kim and I. Kim, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02758C

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