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

Jinwoo Kim, Ikyon Kim

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)89-100
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number1
DOIs
Publication statusPublished - 2017

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (2017R1A2A2A05069364).

Publisher Copyright:
© 2017 The Royal Society of Chemistry.

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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