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Literature DB >> 30393407

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

Abstract

An enantioselective synthesis of the C2-C16 segment of the novel antitumor agent laulimalide is described. The key steps involve a highly diastereoselective allylation, ring-closing olefin metathesis of a homoallylic alcohol derived acrylate ester, a stereoselective anomeric alkylation and an elaboration of an exo-methylene unit by a Julia olefination reaction.

Entities: Chemical Disease

Year: 2002 PMID： 30393407 PMCID： PMC6214628 DOI： 10.1016/S0040-4039(00)00158-1

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

2 in total

1. General Synthesis of alpha-Acetoxy Ethers from Esters by DIBALH Reduction and Acetylation.

Authors: Vilas H. Dahanukar; Scott D. Rychnovsky
Journal: J Org Chem Date: 1996-11-15 Impact factor: 4.354

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

Authors: Arun K Ghosh; Packiarajan Mathivanan; John Cappiello
Journal: Tetrahedron Lett Date: 2000-03-17 Impact factor: 2.415

2 in total

3 in total

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

1. General Synthesis of alpha-Acetoxy Ethers from Esters by DIBALH Reduction and Acetylation.

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

1. Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.

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

3. Enantioselective total synthesis and structural assignment of callyspongiolide.

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

1. General Synthesis of alpha-Acetoxy Ethers from Esters by DIBALH Reduction and Acetylation.

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

1. Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.

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

3. Enantioselective total synthesis and structural assignment of callyspongiolide.

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

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