2015
DOI: 10.1021/acs.orglett.5b01888
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Total Synthesis of Aquatolide

Abstract: A total synthesis of the sesquiterpene lactone aquatolide has been accomplished. The central step is an intramolecular [2 + 2]-photocycloaddition of an allene onto an α,β-unsaturated δ-lactone. Other key steps are an intramolecular Horner-Wadsworth-Emmons reaction to close the lactone and an intramolecular Mukaiyama-type aldol reaction to cyclize the eight-membered ring. Racemic aquatolide has been resolved using preparative HPLC.

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Cited by 52 publications
(53 citation statements)
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“…The structure 153 proposed by Tantillo and co-workers 77 was eventually prepared by Hiemstra and co-workers 77 featuring an intramolecular [2 + 2]-photocycloaddition between an allene and an α,β-unsaturated δ-lactone as the key step to construct its tricyclic core (Scheme 20). 79 The synthesis started with a Ti(O i Pr) 4 promoted cross aldol involving isobutyraldehyde (154) and propargylic aldehyde which required conversion of the product into the corresponding dimetylacetal 155. Esterification of 155 provided the requisite phosphonate 156 and paved the way for the intramolecular Horner-Wadsworth- Emmons reaction which afforded the corresponding α,β-unsaturated-δ-lactone which was finally converted to allenic lactone 157.…”
Section: Aquatolidementioning
confidence: 99%
“…The structure 153 proposed by Tantillo and co-workers 77 was eventually prepared by Hiemstra and co-workers 77 featuring an intramolecular [2 + 2]-photocycloaddition between an allene and an α,β-unsaturated δ-lactone as the key step to construct its tricyclic core (Scheme 20). 79 The synthesis started with a Ti(O i Pr) 4 promoted cross aldol involving isobutyraldehyde (154) and propargylic aldehyde which required conversion of the product into the corresponding dimetylacetal 155. Esterification of 155 provided the requisite phosphonate 156 and paved the way for the intramolecular Horner-Wadsworth- Emmons reaction which afforded the corresponding α,β-unsaturated-δ-lactone which was finally converted to allenic lactone 157.…”
Section: Aquatolidementioning
confidence: 99%
“…1, 2 In the course of this work, the total synthesis of aquatolide was published. 6 Again, the authors provided the original FID, from which we could demonstrate the rapid dereplication of the isolated natural product vs. the synthesized compound. The resulting report 1 demonstrates the power of shared HNMR FIDs and adequate tabular description for the promotion of accurate structural elucidation and reliable dereplication.…”
Section: B Fids Foster Reproducibility and Integritymentioning
confidence: 99%
“…and Ito et al. recently reported the syntheses of aquatolide and naupliolide by constructing the challenging small rings at the beginning of their respective sequences …”
Section: Introductionmentioning
confidence: 99%