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Literature DB >> 17048863

Cycloaddition protocol for the assembly of the hexacyclic framework associated with the kopsifoline alkaloids.

Xuechuan Hong¹, Stefan France, José M Mejía-Oneto, Albert Padwa.

Abstract

An approach to the hexacyclic framework of the kopsifoline alkaloids has been developed and is based on a Rh(II)-catalyzed cyclization-cycloaddition cascade. The resulting [3+2]-cycloadduct was readily converted into the TBS enol ether 23. Oxidation of the primary alcohol present in 23 followed by reaction with CsF afforded compound 24 that contains the complete hexacyclic skeleton of the kopsifolines. [reaction: see text]

Entities: Chemical Gene

Mesh：

Substances：

Year: 2006 PMID： 17048863 PMCID： PMC2475586 DOI： 10.1021/ol062029z

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

14 in total

1. Cascade Processes of Metallo Carbenoids.

Authors: Albert Padwa; M. David Weingarten
Journal: Chem Rev Date: 1996-02-01 Impact factor: 60.622

2. A rhodium carbene cyclization-cycloaddition cascade strategy toward the pseudolaric acids.

Authors: P Chiu; B Chen; K F Cheng
Journal: Org Lett Date: 2001-05-31 Impact factor: 6.005

3. Intramolecular [3 + 2]-cycloaddition reaction of push-pull dipoles across heteroaromatic pi-systems.

Authors: José M Mejía-Oneto; Albert Padwa
Journal: Org Lett Date: 2004-09-16 Impact factor: 6.005

4. Application of the Rh(II) cyclization/cycloaddition cascade for the total synthesis of (+/-)-aspidophytine.

Authors: José M Mejía-Oneto; Albert Padwa
Journal: Org Lett Date: 2006-07-20 Impact factor: 6.005

5. Cycloaddition chemistry of 2-vinyl-substituted indoles and related heteroaromatic systems.

Authors: Albert Padwa; Stephen M Lynch; José M Mejía-Oneto; Hongjun Zhang
Journal: J Org Chem Date: 2005-03-18 Impact factor: 4.354

6. Utilization of the Intramolecular Cycloaddition-Cationic pi-Cyclization of an Isomünchnone Derivative for the Synthesis of (+/-)-Lycopodine.

Authors: Albert Padwa; Michael A. Brodney; Joseph P. Marino; Scott M. Sheehan
Journal: J Org Chem Date: 1997-01-10 Impact factor: 4.354

7. Synthesis of the Pentacyclic Skeleton of the Aspidosperma Alkaloids Using Rhodium Carbenoids as Reactive Intermediates.

Authors: Albert Padwa; Alan T. Price
Journal: J Org Chem Date: 1998-02-06 Impact factor: 4.354

2. Total syntheses of (-)-kopsifoline D and (-)-deoxoapodine: divergent total synthesis via late-stage key strategic bond formation.

Authors: Kiyoun Lee; Dale L Boger
Journal: J Am Chem Soc Date: 2014-02-17 Impact factor: 15.419

2 in total

Cycloaddition protocol for the assembly of the hexacyclic framework associated with the kopsifoline alkaloids.

1. Cascade Processes of Metallo Carbenoids.

2. A rhodium carbene cyclization-cycloaddition cascade strategy toward the pseudolaric acids.

3. Intramolecular [3 + 2]-cycloaddition reaction of push-pull dipoles across heteroaromatic pi-systems.

4. Application of the Rh(II) cyclization/cycloaddition cascade for the total synthesis of (+/-)-aspidophytine.

5. Cycloaddition chemistry of 2-vinyl-substituted indoles and related heteroaromatic systems.

6. Utilization of the Intramolecular Cycloaddition-Cationic pi-Cyclization of an Isomünchnone Derivative for the Synthesis of (+/-)-Lycopodine.

7. Synthesis of the Pentacyclic Skeleton of the Aspidosperma Alkaloids Using Rhodium Carbenoids as Reactive Intermediates.

8. Stereocontrolled syntheses of the nemorensic acids using 6-diazoheptane-2,5-dione in carbonyl ylide cycloadditions.

9. A tandem metal carbene cyclization-cycloaddition approach to the pseudolaric acids.

10. A new strategy toward indole alkaloids involving an intramolecular cycloaddition/rearrangement cascade.

1. A Dipolar Cycloaddition Approach Toward the Kopsifoline Alkaloid Framework.

2. Total syntheses of (-)-kopsifoline D and (-)-deoxoapodine: divergent total synthesis via late-stage key strategic bond formation.