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Synthesis 2018; 50(03): 658-662
DOI: 10.1055/s-0036-1590944
paper
© Georg Thieme Verlag Stuttgart · New York

First Total Synthesis of (±)-Rhodoconferimide

Kailas R. Pandhade
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India   Email: np.argade@ncl.res.in
,
Narshinha P. Argade  *
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India   Email: np.argade@ncl.res.in
› Author Affiliations
Further Information

Publication History

Received: 24 August 2017

Accepted after revision: 05 October 2017

Publication Date:
06 November 2017 (online)

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Abstract

Starting from vanillin and dimethyl maleate, a concise and efficient racemic total synthesis of the potent antioxidant marine natural product (±)-rhodoconferimide has been carried out via the Wittig reaction, catalytic hydrogenation, selective brominations, and imide formation. An appropriate regioselective double bromination of the aromatic ring was a key step in the synthesis.

Key words

vanillin - bromination - (±)-rhodoconferimide - antioxidants - natural products - total synthesis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590944. NMR spectra of all the synthesized compounds are included.
  • Supporting Information
 

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