A biomimetic cascade for the formation of the methyl [2(5H)-furanylidene]ethanoate core of spongosoritin A and the gracilioethers

Matthew Norris; Michael Perkins

doi:10.1016/j.tet.2013.09.006

A biomimetic cascade for the formation of the methyl [2(5H)-furanylidene]ethanoate core of spongosoritin A and the gracilioethers

Matthew Norris, Michael Perkins

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

The polyketide secondary metabolites spongosoritin A and gracilioethers A-C contain a unique methyl [2(5H)-furanylidene]ethanoate core. A synthetic model of a suspected biosynthetic intermediate to these natural products was constructed in seven steps and 48% overall yield. This model undergoes a facile cyclisation/double dehydration cascade to give the desired furanylidene motif, with the required (2Z) isomer obtained in >90 dr when an ethyl substituent is located at C3′ of the furanylidene.

Original language	English
Pages (from-to)	9813-9818
Number of pages	6
Journal	Tetrahedron
Volume	69
Issue number	46
DOIs	https://doi.org/10.1016/j.tet.2013.09.006
Publication status	Published - 18 Nov 2013

Keywords

Cyclisation/dehydration cascade
Gracilioether
Methyl [2(5H)-furanylidene]ethanoate
Sodio-lithio dianion enolate

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10.1016/j.tet.2013.09.006

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title = "A biomimetic cascade for the formation of the methyl [2(5H)-furanylidene]ethanoate core of spongosoritin A and the gracilioethers",

abstract = "The polyketide secondary metabolites spongosoritin A and gracilioethers A-C contain a unique methyl [2(5H)-furanylidene]ethanoate core. A synthetic model of a suspected biosynthetic intermediate to these natural products was constructed in seven steps and 48% overall yield. This model undergoes a facile cyclisation/double dehydration cascade to give the desired furanylidene motif, with the required (2Z) isomer obtained in >90 dr when an ethyl substituent is located at C3′ of the furanylidene.",

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AU - Perkins, Michael

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AB - The polyketide secondary metabolites spongosoritin A and gracilioethers A-C contain a unique methyl [2(5H)-furanylidene]ethanoate core. A synthetic model of a suspected biosynthetic intermediate to these natural products was constructed in seven steps and 48% overall yield. This model undergoes a facile cyclisation/double dehydration cascade to give the desired furanylidene motif, with the required (2Z) isomer obtained in >90 dr when an ethyl substituent is located at C3′ of the furanylidene.

KW - Cyclisation/dehydration cascade

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KW - Methyl [2(5H)-furanylidene]ethanoate

KW - Sodio-lithio dianion enolate

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SP - 9813

EP - 9818

JO - Tetrahedron

JF - Tetrahedron

IS - 46

ER -

A biomimetic cascade for the formation of the methyl [2(5H)-furanylidene]ethanoate core of spongosoritin A and the gracilioethers

Abstract

Keywords

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