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Literature DB >> 17975920

A general method for the synthesis of nonracemic trans-epoxides: concise syntheses of trans-epoxide-containing insect sex pheromones.

Abstract

A general method for the synthesis of chiral nonracemic trans-epoxides has been developed that provides rapid access to alkyl-, alkenyl-, alkynyl-, and phenyl-substituted trans-epoxides from aldehydes. This methodology has also been applied in concise and high-yielding syntheses of both trans-epoxide containing insect sex pheromones.

Entities: Chemical

Mesh：

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Year: 2007 PMID： 17975920 DOI： 10.1021/ol702273n

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

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Cited

6 in total

1. Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

Authors: Jakub Saadi; Matsujiro Akakura; Hisashi Yamamoto
Journal: J Am Chem Soc Date: 2011-08-18 Impact factor: 15.419

2. A Chlorine-Atom-Controlled Terminal-Epoxide-Initiated Bicyclization Cascade Enables a Synthesis of the Potent Cytotoxins Haterumaimides J and K.

Authors: Sharon E Michalak; Sangkil Nam; David M Kwon; David A Horne; Christopher D Vanderwal
Journal: J Am Chem Soc Date: 2019-06-03 Impact factor: 15.419

3. Design and Synthesis of Fluorophore-Tagged Disparlure Enantiomers to Study Pheromone Enantiomer Discrimination in the Pheromone-Binding Proteins from the Gypsy Moth, Lymantria dispar.

Authors: Govardhana R Pinnelli; Erika Plettner
Journal: J Chem Ecol Date: 2021-10-11 Impact factor: 2.626

A general method for the synthesis of nonracemic trans-epoxides: concise syntheses of trans-epoxide-containing insect sex pheromones.

1. Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

2. A Chlorine-Atom-Controlled Terminal-Epoxide-Initiated Bicyclization Cascade Enables a Synthesis of the Potent Cytotoxins Haterumaimides J and K.

3. Design and Synthesis of Fluorophore-Tagged Disparlure Enantiomers to Study Pheromone Enantiomer Discrimination in the Pheromone-Binding Proteins from the Gypsy Moth, Lymantria dispar.

4. β-Siloxy-α-haloketones through highly diastereoselective single and double mukaiyama aldol reactions.

Review 5. Stereoselective Halogenation in Natural Product Synthesis.

6. Enantio and diastereoselective addition of phenylacetylene to racemic α-chloroketones.