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Solid phase versus solution phase synthesis of heterocyclic macrocycles.

ABSTRACT: Comparing a solution phase route to a solid phase route in the synthesis of the cytotoxic natural product urukthapelstatin A (Ustat A) confirmed that a solid phase method is superior. The solution phase approach was tedious and involved cyclization of a ridged heterocyclic precursor, while solid phase allowed the rapid generation of a flexible linear peptide. Cyclization of the linear peptide was facile and subsequent generation of three oxazoles located within the structure of Ustat A proved relatively straightforward. Given the ease with which the oxazole Ustat A precursor is formed via our solid phase approach, this route is amenable to rapid analog synthesis.

SUBMITTER: Kim SJ

PROVIDER: S-EPMC6269862 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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Solid phase versus solution phase synthesis of heterocyclic macrocycles.

Kim Seong Jong SJ McAlpine Shelli R SR

Molecules (Basel, Switzerland) 20130116 1

Comparing a solution phase route to a solid phase route in the synthesis of the cytotoxic natural product urukthapelstatin A (Ustat A) confirmed that a solid phase method is superior. The solution phase approach was tedious and involved cyclization of a ridged heterocyclic precursor, while solid phase allowed the rapid generation of a flexible linear peptide. Cyclization of the linear peptide was facile and subsequent generation of three oxazoles located within the structure of Ustat A proved re ...[more]

PMID: 23325099

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