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Literature DB >> 16448105

Total synthesis of (+/-)-welwitindolinone a isonitrile.

Sarah E Reisman¹, Joseph M Ready, Atsushi Hasuoka, Catherine J Smith, John L Wood.

Abstract

A highly stereoselective total synthesis of the alkaloid natural product welwitindolinone A isonitrile has been completed. The synthesis utilizes a chloronium ion mediated semi-pinacol rearrangement to simultaneously install the C10 quaternary center and neopentyl chlorine and a novel anionic cyclization to construct the spiro-oxindole with complete stereocontrol.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2006 PMID： 16448105 DOI： 10.1021/ja057640s

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

32 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

2. Enantiospecific total synthesis of the hapalindoles, fischerindoles, and welwitindolinones via a redox economic approach.

Authors: Jeremy M Richter; Yoshihiro Ishihara; Takeshi Masuda; Brandon W Whitefield; Tomás Llamas; Antti Pohjakallio; Phil S Baran
Journal: J Am Chem Soc Date: 2008-12-31 Impact factor: 15.419

10. A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles.

Authors: Kay M Brummond; Joshua M Osbourn
Journal: Beilstein J Org Chem Date: 2010-04-08 Impact factor: 2.883

Total synthesis of (+/-)-welwitindolinone a isonitrile.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. Enantiospecific total synthesis of the hapalindoles, fischerindoles, and welwitindolinones via a redox economic approach.

3. Antimicrobial ambiguine isonitriles from the cyanobacterium Fischerella ambigua.

4. Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate.

5. Enantiospecific total synthesis of N-methylwelwitindolinone D isonitrile.

6. An approach to the total synthesis of welwistatin.

7. Total synthesis of the chlorine-containing hapalindoles K, A, and G.

8. Approaches to N-methylwelwitindolinone C isothiocyanate: facile synthesis of the tetracyclic core.

9. Access to a welwitindolinone core using sequential cycloadditions.

10. A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles.