Limits...
Tandem C-H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (-)-brussonol and (-)-przewalskine E.

Jiao ZW, Tu YQ, Zhang Q, Liu WX, Zhang SY, Wang SH, Zhang FM, Jiang S - Nat Commun (2015)

Bottom Line: Development of efficient tandem reactions to build useful compounds and apply them to the synthesis of natural products is not only a significant challenge but also an important goal for chemists.This method allows the efficient construction of tricyclic benzoxa[3.2.1]octanes with a wide substrate scope.We employ this tandem reaction to achieve the asymmetric total syntheses of (-)-brussonol and (-)-przewalskine E.

View Article: PubMed Central - PubMed

Affiliation: State Key Laboratory of Applied Organic Chemistry &College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.

ABSTRACT
Natural products are a vital source of lead compounds in drug discovery. Development of efficient tandem reactions to build useful compounds and apply them to the synthesis of natural products is not only a significant challenge but also an important goal for chemists. Here we describe a tandem C-H oxidation/cyclization/rearrangement of isochroman-derived allylic silylethers, promoted by DDQ and InCl3. This method allows the efficient construction of tricyclic benzoxa[3.2.1]octanes with a wide substrate scope. We employ this tandem reaction to achieve the asymmetric total syntheses of (-)-brussonol and (-)-przewalskine E.

No MeSH data available.


Representative natural products containing benzoxa[3.2.1]octane skeleton and approaches to it.(a) Selected bioactive natural products having benzoxa[3.2.1]octane skeleton. (b) Previous methods for construction of benzoxa[3.2.1]octane skeleton. (c) Our synthetic proposal via a tandem C–H oxidation/cyclization/rearrangement reaction.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4557391&req=5

f1: Representative natural products containing benzoxa[3.2.1]octane skeleton and approaches to it.(a) Selected bioactive natural products having benzoxa[3.2.1]octane skeleton. (b) Previous methods for construction of benzoxa[3.2.1]octane skeleton. (c) Our synthetic proposal via a tandem C–H oxidation/cyclization/rearrangement reaction.

Mentions: The strained tricyclic benzoxa[3.2.1]octane skeleton exists in numerous bioactive and pharmaceutical molecules such as przewalskone1 and brussonol2, and it is a useful building block in organic synthesis such as for producing platensimycin3 (Fig. 1a). In recent decades, the significant biological activity and potential pharmaceutical value of molecules with this skeleton have driven chemists to devise several methods for constructing it (Fig. 1b)34567891011121314. Nevertheless, more efficient and practical methods are needed.


Tandem C-H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (-)-brussonol and (-)-przewalskine E.

Jiao ZW, Tu YQ, Zhang Q, Liu WX, Zhang SY, Wang SH, Zhang FM, Jiang S - Nat Commun (2015)

Representative natural products containing benzoxa[3.2.1]octane skeleton and approaches to it.(a) Selected bioactive natural products having benzoxa[3.2.1]octane skeleton. (b) Previous methods for construction of benzoxa[3.2.1]octane skeleton. (c) Our synthetic proposal via a tandem C–H oxidation/cyclization/rearrangement reaction.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4557391&req=5

f1: Representative natural products containing benzoxa[3.2.1]octane skeleton and approaches to it.(a) Selected bioactive natural products having benzoxa[3.2.1]octane skeleton. (b) Previous methods for construction of benzoxa[3.2.1]octane skeleton. (c) Our synthetic proposal via a tandem C–H oxidation/cyclization/rearrangement reaction.
Mentions: The strained tricyclic benzoxa[3.2.1]octane skeleton exists in numerous bioactive and pharmaceutical molecules such as przewalskone1 and brussonol2, and it is a useful building block in organic synthesis such as for producing platensimycin3 (Fig. 1a). In recent decades, the significant biological activity and potential pharmaceutical value of molecules with this skeleton have driven chemists to devise several methods for constructing it (Fig. 1b)34567891011121314. Nevertheless, more efficient and practical methods are needed.

Bottom Line: Development of efficient tandem reactions to build useful compounds and apply them to the synthesis of natural products is not only a significant challenge but also an important goal for chemists.This method allows the efficient construction of tricyclic benzoxa[3.2.1]octanes with a wide substrate scope.We employ this tandem reaction to achieve the asymmetric total syntheses of (-)-brussonol and (-)-przewalskine E.

View Article: PubMed Central - PubMed

Affiliation: State Key Laboratory of Applied Organic Chemistry &College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.

ABSTRACT
Natural products are a vital source of lead compounds in drug discovery. Development of efficient tandem reactions to build useful compounds and apply them to the synthesis of natural products is not only a significant challenge but also an important goal for chemists. Here we describe a tandem C-H oxidation/cyclization/rearrangement of isochroman-derived allylic silylethers, promoted by DDQ and InCl3. This method allows the efficient construction of tricyclic benzoxa[3.2.1]octanes with a wide substrate scope. We employ this tandem reaction to achieve the asymmetric total syntheses of (-)-brussonol and (-)-przewalskine E.

No MeSH data available.