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Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
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Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy...
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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...
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The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Hydroxyl-substituted ladder polyethers via selective tandem epoxidation/cyclization sequence.

Lara C Czabaniuk1, Timothy F Jamison

  • 1Department of Chemistry, Massachusetts Institute of Technology , 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.

Organic Letters
|February 4, 2015
PubMed
Summary
This summary is machine-generated.

A novel synthetic method efficiently creates hydroxyl-substituted tetrahydropyrans using titanium catalysis. This approach was successfully applied to synthesize a key fragment of the marine toxin yessotoxin.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Tetrahydropyrans are common structural motifs in natural products.
  • Efficient and selective synthesis of substituted tetrahydropyrans remains a challenge.
  • Yessotoxin is a marine ladder polyether with significant biological activity.

Purpose of the Study:

  • To develop a new, highly selective method for synthesizing hydroxyl-substituted tetrahydropyrans.
  • To demonstrate the utility of this method in synthesizing a complex natural product fragment.

Main Methods:

  • Diastereoselective epoxidation using titanium(IV) isopropoxide and diethyl tartrate.
  • In situ epoxide activation and endo-cyclization.
  • Application of the method to synthesize the HIJ ring fragment of yessotoxin.

Main Results:

  • The developed method provides high efficiency and excellent regioselectivity.
  • Successfully synthesized the HIJ ring fragment of yessotoxin.
  • The two-stage tactic proved effective for complex molecule synthesis.

Conclusions:

  • A new and highly selective synthetic route to hydroxyl-substituted tetrahydropyrans has been established.
  • This method offers a powerful tool for the synthesis of complex molecules, including natural products.
  • The synthesis of the yessotoxin fragment highlights the practicality and efficiency of the developed methodology.