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Literature DB >> 19259600

Bridgehead enolates and bridgehead alkenes in a welwistatin model series.

Valerie Boissel¹, Nigel S Simpkins, Gurdip Bhalay, Alexander J Blake, William Lewis.

Abstract

Bridgehead metallation is possible in a ketone having the welwistatin skeleton, and this facilitates installation of the isothiocyanate function present in the natural product, and also enables synthesis of remarkable bridgehead alkenes.

Entities: Chemical

Mesh：

Substances：

Year: 2009 PMID： 19259600 DOI： 10.1039/b820674k

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

12 in total

1. 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

2. 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

3. 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

4. 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

Bridgehead enolates and bridgehead alkenes in a welwistatin model series.

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

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

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

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

5. Total synthesis of N-methylwelwitindolinone D isonitrile.

6. Total synthesis of oxidized welwitindolinones and (-)-N-methylwelwitindolinone C isonitrile.

7. Synthesis of functionalized cyclohexenone core of welwitindolinones via rhodium-catalyzed [5 + 1] cycloaddition.

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.