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Literature DB >> 30344352

SYNTHETIC STUDIES OF ANTITUMOR MACROLIDE LAULIMALIDE: ENANTIOSELECTIVE SYNTHESIS OF THE C₃-C₁₄ SEGMENT BY A CATALYTIC HETERO DIELS-ALDER STRATEGY.

Arun K Ghosh¹, Packiarajan Mathivanan¹, John Cappiello¹.

Abstract

The C3-C14 segment of the novel antitumor agent laulimalide has been constructed enantioselectively by utilizing a catalytic asymmetric hetero Diels-Alder reaction of benzyloxyacetaldehyde and Danishefsky's diene followed by Ferrier rearrangement and asymmetric conjugate reaction as the key steps.

Entities: Chemical Disease

Year: 2000 PMID： 30344352 PMCID： PMC6195360 DOI： 10.1016/S0040-4039(97)00416-4

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

2 in total

1. Studies toward a Synthesis of Epothilone A: Use of Hydropyran Templates for the Management of Acyclic Stereochemical Relationships.

Authors: Dongfang Meng; Erik J. Sorensen; Peter Bertinato; Samuel J. Danishefsky
Journal: J Org Chem Date: 1996-11-15 Impact factor: 4.354

2. Studies toward a Synthesis of Epothilone A: Stereocontrolled Assembly of the Acyl Region and Models for Macrocyclization.

Authors: Peter Bertinato; Erik J. Sorensen; Dongfang Meng; Samuel J. Danishefsky
Journal: J Org Chem Date: 1996-11-15 Impact factor: 4.354

2 in total

7 in total

SYNTHETIC STUDIES OF ANTITUMOR MACROLIDE LAULIMALIDE: ENANTIOSELECTIVE SYNTHESIS OF THE C₃-C₁₄ SEGMENT BY A CATALYTIC HETERO DIELS-ALDER STRATEGY.

1. Studies toward a Synthesis of Epothilone A: Use of Hydropyran Templates for the Management of Acyclic Stereochemical Relationships.

2. Studies toward a Synthesis of Epothilone A: Stereocontrolled Assembly of the Acyl Region and Models for Macrocyclization.

1. Asymmetric hetero Diels-Alder route to quaternary carbon centers: synthesis of (-)-malyngolide.

2. An enantioselective synthesis of the C₂-C₁₆ segment of antitumor macrolide laulimalide¹.

3. Synthetic studies of antitumor macrolide laulimalide: a stereoselective synthesis of the C₁₇-C₂₈ segment.

4. cis-1-Aminoindan-2-ol in Asymmetric Syntheses.

5. Total Synthesis of (-)-Laulimalide.

6. C ₂-Symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis.

7. A macrolactonization-based strategy to obtain microtuble-stabilizing agent (-)-laulimalide.