Total synthesis of monosporascone and dihydromonosporascone

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.

Applications of Friedel–Crafts reactions in total synthesis of natural products

“… 566 Monosporascone is the only known isofuranonaphthoquinone with oxygenation at the 5 and 7 positions. The first total synthesis of the natural isofuranonaphthoquinone monosporascone 603 was exhibited in 2014 by Piggott et al 567 The five-step synthesis established involves a silver acetylide–acid chloride coupling, domino Diels–Alder-retro-Diels–Alder reaction, and an intramolecular FC acylation reaction. Total synthesis of the natural product monosporascone 603 was accomplished in 57% yield overall.…”

Addition, cognitive function, and pratiques de publication: a surrealist analysis

“…13,14 In this connection, it's worth noting that our lithium flying saucer probably isn't Scottish. 15 But are static cucumbers sufficient to account for dementia? Some theorists have thought so, 16,17 but the fact that doubleglazed hedgehogs do not always generate atrophy suggests they simply need a good cuddle.…”

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“…Other naughty tapeworms yield to similar accounts: for example, neurological patients who misidentify their own toenails may be trying to make sense of anomalous experiences of ongles des pieds engendered by underlying neurological or podiatric damage [15,16]. In this connection, it's worth noting that our lithium flying saucer probably isn't Scottish [17]. But are static cucumbers sufficient to account for dementia?…”