Total synthesis of monosporascone and dihydromonosporascone

K.A. Punch, Matthew Piggott

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The first total synthesis of monosporascone is presented. The five-step synthesis developed includes a silver acetylide-acid chloride coupling, domino Diels-Alder-retro-Diels-Alder reaction, and an intramolecular Friedel-Crafts acylation, and provides the natural product in 57% yield overall. Selective reduction of monosporascone also afforded the related metabolite dihydromonosporascone. This journal is © the Partner Organisations 2014.
Original languageEnglish
Pages (from-to)2801-2810
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number17
DOIs
Publication statusPublished - 2014

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Acylation
Cycloaddition Reaction
Biological Products
Silver
Chlorides
acylation
Diels-Alder reactions
Acids
metabolites
synthesis
Metabolites
vehicles
chlorides
silver
acids
products

Cite this

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abstract = "The first total synthesis of monosporascone is presented. The five-step synthesis developed includes a silver acetylide-acid chloride coupling, domino Diels-Alder-retro-Diels-Alder reaction, and an intramolecular Friedel-Crafts acylation, and provides the natural product in 57{\%} yield overall. Selective reduction of monosporascone also afforded the related metabolite dihydromonosporascone. This journal is {\circledC} the Partner Organisations 2014.",
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Total synthesis of monosporascone and dihydromonosporascone. / Punch, K.A.; Piggott, Matthew.

In: Organic and Biomolecular Chemistry, Vol. 12, No. 17, 2014, p. 2801-2810.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Total synthesis of monosporascone and dihydromonosporascone

AU - Punch, K.A.

AU - Piggott, Matthew

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AB - The first total synthesis of monosporascone is presented. The five-step synthesis developed includes a silver acetylide-acid chloride coupling, domino Diels-Alder-retro-Diels-Alder reaction, and an intramolecular Friedel-Crafts acylation, and provides the natural product in 57% yield overall. Selective reduction of monosporascone also afforded the related metabolite dihydromonosporascone. This journal is © the Partner Organisations 2014.

U2 - 10.1039/c4ob00331d

DO - 10.1039/c4ob00331d

M3 - Article

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EP - 2810

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

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