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Chemistry - Organic Chemistry | Stereoselective Syntheses of Tetrahydropyrans - Applications to the Synthesis of (+)-Leucascandrolide

Stereoselective Syntheses of Tetrahydropyrans

Applications to the Synthesis of (+)-Leucascandrolide A, (+)-Dactylolide and (±)-Diospongin A

Series: Springer Theses

Lee, Kiyoun

2014, XIX, 184 p. 256 illus., 12 illus. in color.

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  • Nominated as an outstanding Ph.D. thesis by Duke University, USA
  • Pursues a clearly structured and easy-to-follow methodology
  • Provides straightforward figures of target molecules
  • Includes easy-to-find references for further reading
In his thesis, Kiyoun Lee describes his studies into tandem and organocatalytic oxa-conjugate addition reactions for the synthesis of complex tetrahydropyrans (THP). Readers gain insight into the new methods Lee employs for the synthesis of biologically interesting natural products including (+)-leucascandrolide A, (+)-dactylolide, and (±)-diospongin A. The reactions Lee investigates are applicable to a broad range of substrates and proceed with excellent stereoselectivity. Moreover, the methodologies allow the synthesis of a wide range of THP-containing compounds. The development of reactions, such as those discussed by Lee, has the potential to impact natural product synthesis, pharmaceutical development and chemical biology.

Content Level » Research

Keywords » (+)-Dactylolide - (+)-Leucascandrolide A - (±)-Diospongin A - Gem-disubstituent Effect - Tandem Cross-metathesis/thermal SN2′ - Tandem and Organocatalytic Oxa-conjugate Addition - Tetrahydropyran

Related subjects » Industrial Chemistry and Chemical Engineering - Organic Chemistry - Pharmacology & Toxicology

Table of contents 

Introduction.- Significance.- General Approaches to the Synthesis of Substituted Tetrahydropyrans.- Stereoselective Synthesis of Tetrahydropyrans via Tandem and Organocatalytic Oxa-Conjugate Addition Reactions.- Introduction.- Preliminary Study.- Result and Discussion.- Synthesis of 4-Hydroxy-2,6-cis-Tetrahydropyrans via Tandem Cross-Metathesis/Thermal SN2′ Reaction.

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