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Literature DB >> 23976796

Studies toward welwitindolinones: formal syntheses of N-methylwelwitindolinone C isothiocyanate and related natural products.

Tsung-Hao Fu¹, William T McElroy, Mariam Shamszad, Richard W Heidebrecht, Brian Gulledge, Stephen F Martin.

Abstract

The formal syntheses of N-methylwelwitindolinone C isothiocyanate (4) and several other welwitindolinones 5-8 were achieved by the independent synthesis of 79. The synthesis featured a Lewis acid-mediated coupling between a heteroaryl carbinol and bis-TMS enol ether, an intramolecular enolate arylation, and an unprecedented intramolecular allylic alkylation of a γ-acyloxyenone.

Entities: CellLine Chemical Disease Gene Species

Keywords: Alkaloids; Allylic alkylation; Enolate arylation; Lewis acid-mediated coupling; Welwitindolinones

Year: 2013 PMID： 23976796 PMCID： PMC3748834 DOI： 10.1016/j.tet.2013.03.010

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

47 in total

1. STUDIES ON STEROIDAL COMPOUNDS. X. PREPARATION OF 17BETA-CHLORO STEROIDS.

Authors: H MORI; K TSUNEDA
Journal: Chem Pharm Bull (Tokyo) Date: 1963-11 Impact factor: 1.645

2. Total synthesis: Welwitindolinone is well worth it.

Authors: John L Wood
Journal: Nat Chem Date: 2012-04-23 Impact factor: 24.427

3. Bridgehead enolates and bridgehead alkenes in a welwistatin model series.

Authors: Valerie Boissel; Nigel S Simpkins; Gurdip Bhalay; Alexander J Blake; William Lewis
Journal: Chem Commun (Camb) Date: 2009-01-21 Impact factor: 6.222

4. 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

5. Stereocontrolled synthesis of 20,21-dihydro N-methylwelwitindolinone B isothiocyanate.

Authors: Vikram Bhat; Viresh H Rawal
Journal: Chem Commun (Camb) Date: 2011-07-27 Impact factor: 6.222

6. 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

7. Total synthesis of N-methylwelwitindolinone D isonitrile.

Authors: Vikram Bhat; Kevin M Allan; Viresh H Rawal
Journal: J Am Chem Soc Date: 2011-03-29 Impact factor: 15.419

8. Pd/P(t-Bu)(3): a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides.

Authors: Adam F Littke; Lothar Schwarz; Gregory C Fu
Journal: J Am Chem Soc Date: 2002-06-05 Impact factor: 15.419

9. Rapid access to the Welwitindolinone alkaloid skeleton by cyclization of indolecarboxaldehyde substituted cyclohexanones.

Authors: Jérôme Baudoux; Alexander J Blake; Nigel S Simpkins
Journal: Org Lett Date: 2005-09-15 Impact factor: 6.005

Studies toward welwitindolinones: formal syntheses of N-methylwelwitindolinone C isothiocyanate and related natural products.

1. STUDIES ON STEROIDAL COMPOUNDS. X. PREPARATION OF 17BETA-CHLORO STEROIDS.

2. Total synthesis: Welwitindolinone is well worth it.

3. Bridgehead enolates and bridgehead alkenes in a welwistatin model series.

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

5. Stereocontrolled synthesis of 20,21-dihydro N-methylwelwitindolinone B isothiocyanate.

6. An approach to the total synthesis of welwistatin.

7. Total synthesis of N-methylwelwitindolinone D isonitrile.

8. Pd/P(t-Bu)(3): a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides.

9. Rapid access to the Welwitindolinone alkaloid skeleton by cyclization of indolecarboxaldehyde substituted cyclohexanones.

10. Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles.

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

2. Natural Products and Their Mimics as Targets of Opportunity for Discovery.

3. Concise total synthesis of (±)-actinophyllic acid.

4. Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation.

5. Total synthesis of (-)-N-methylwelwitindolinone B isothiocyanate via a chlorinative oxabicycle ring-opening strategy.