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Literature DB >> 11554828

Aryllead(IV) reagents in synthesis: formation of the C11 quaternary center of N-methylwelwitindolinone C isothiocyanate.

Abstract

The reaction of lead(IV) 4-indolyl triacetate with substituted methyl 2-oxo-1-cyclohexanecarboxylates has been investigated as a route to the natural product N-methylwelsitindolinone C isothiocyanate. Reaction of lead(IV) reagent 18 with beta-ketoester 20 affords the desired coupled material in excellent yield and diastereoselectivity. Reaction: see text.

Entities: Chemical Gene

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Year: 2001 PMID： 11554828 DOI： 10.1021/ol016379r

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

20 in total

1. 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

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

Authors: Alexander D Huters; Kyle W Quasdorf; Evan D Styduhar; Neil K Garg
Journal: J Am Chem Soc Date: 2011-08-11 Impact factor: 15.419

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

Authors: Evan D Styduhar; Alexander D Huters; Nicholas A Weires; Neil K Garg
Journal: Angew Chem Int Ed Engl Date: 2013-10-02 Impact factor: 15.336

4. An approach to the total synthesis of welwistatin.

Authors: Thomas J Greshock; Raymond L Funk
Journal: Org Lett Date: 2006-06-08 Impact factor: 6.005

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

Authors: Richard W Heidebrecht; Brian Gulledge; Stephen F Martin
Journal: Org Lett Date: 2010-06-04 Impact factor: 6.005

6. Directed oxidative cyclizations to C2- or C4-positions of indole: efficient construction of the bicyclo[4.3.1]decane core of welwitindolinones.

Authors: Vikram Bhat; James A Mackay; Viresh H Rawal
Journal: Org Lett Date: 2011-05-26 Impact factor: 6.005

Aryllead(IV) reagents in synthesis: formation of the C11 quaternary center of N-methylwelwitindolinone C isothiocyanate.

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

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

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

4. An approach to the total synthesis of welwistatin.

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

6. Directed oxidative cyclizations to C2- or C4-positions of indole: efficient construction of the bicyclo[4.3.1]decane core of welwitindolinones.

7. Total synthesis of N-methylwelwitindolinone D isonitrile.

8. Lessons Learned while Traversing the Welwitindolinone Alkaloids Obstacle Course.

9. Synthesis of the bicyclic welwitindolinone core via an alkylation/cyclization cascade reaction.

10. Formal syntheses of naturally occurring welwitindolinones.