Publication:
Synthesis of integerrimide A by an on-resin tandem Fmoc-deprotection- macrocyclisation approach

Issued Date

2013-01-01

Resource Type

Article

ISSN

14770520

DOI

10.1039/c3ob41447g

Other identifier(s)

2-s2.0-84886408136

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Organic and Biomolecular Chemistry. Vol.11, No.44 (2013), 7760-7767

Suggested Citation

Sirirat Kumarn, Nitirat Chimnoi, Somsak Ruchirawat Synthesis of integerrimide A by an on-resin tandem Fmoc-deprotection- macrocyclisation approach. Organic and Biomolecular Chemistry. Vol.11, No.44 (2013), 7760-7767. doi:10.1039/c3ob41447g Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/31411

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Title

Synthesis of integerrimide A by an on-resin tandem Fmoc-deprotection- macrocyclisation approach

Author(s)

Sirirat Kumarn
 Nitirat Chimnoi
 Somsak Ruchirawat

Other Contributor(s)

Mahidol University
 Chulabhorn Research Institute
 South Carolina Commission on Higher Education

Abstract

A solid-phase total synthesis of integerrimide A (1) is reported. This work employs a safety-catch linker which enables head-to-tail cyclisation of the required linear peptide 6 as a method of cleaving the peptide from the solid support, and highlights a new tandem approach to direct macrocyclisation. It provides access to useful quantities of 1 in 16 steps and 19% overall yield, based on the manufacturer's stated resin substitution from commercially available materials, and also verifies the absolute stereochemistry of the natural product. © The Royal Society of Chemistry 2013.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry

Availability

URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/31411

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Scopus 2011-2015