A New Synthetic Approach Toward (+)-Ambruticin Analogs: Preparation of a C10–C11cis-Isomer Fragment

Michelet, Véronique; Adiey, Kouacou; Bulic, Bruno; Genêt, Jean‐Pierre; Dujardin, Gilles; Rossignol, Sandrine; Brown, Eric; Toupet, Loı̈c

doi:10.1002/(sici)1099-0690(199911)1999:11<2885::aid-ejoc2885>3.0.co;2-j

Cited by 16 publications

(4 citation statements)

References 20 publications

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“…Taking the advantage of chiral chromium catalyst 24 [12c] or the chiral dienophile 25 [20] (Scheme 4), two independent groups reported the preparation of functionalized tetrahydropyran. The highly enantio-and diastereoselective chromium-catalyzed HDA between aldehyde 20 and diene 21 provided dihydropyran 22 in 97% ee.…”

Section: Hetero-diels-alder Strategymentioning

confidence: 99%

“…A key dihydropyran intermediate was also expected to be stereoselectively and asymmetrically delivered by means of an inverse-electron demand hetero Diels-Alder [20,21]. The Eu(fod) 3 -catalyzed heterocycloaddition of chiral vinyl ether 25, derived from (R)-mandelic acid, followed by stereoselective hydroboration/oxidation and chiral moiety removal afforded a 2/1 mixture of lactols 27.…”

Section: Hetero-diels-alder Strategymentioning

confidence: 99%

“…Nevertheless, the long synthetic pathway involving 17 steps prompted us to envisage a new strategy. In collaboration with Dujardin's group, a more straightforward route to the A-ring was optimized using a key hetero Diels-Alder reaction [20] (Scheme 4). The A-ring derivative 13 was prepared in 11 high-yielding steps.…”

Section: Our Group's Partial Synthesismentioning

confidence: 99%

“…The resulting alcohol was then converted into the corresponding benzoate epi-69 using 2,4-dichlorobenzoyl chloride. The last step of cyclopropanation was conducted with in situ preformed Pd(dppe) 2 as catalyst and DBU as base, and led exclusively to the cis disubstituted cyclopropane epi-70, a C-10 epimer of the western part of ambruticin [20].…”

Section: Our Group's Partial Synthesismentioning

confidence: 99%

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An Overview of Synthetic and Biological Studies of Ambruticin and Analogues

Michelet¹,

Genêt

2005

COC

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Ambruticin is a unique example of antibiotics isolated from the fermentation media of gliding bacteria. Since the last decade, it has emerged as one of the most intensively studied derivative due to its oral antibiotic properties and due to its unique architecture. This structurally exceptional molecule bearing ten stereogenic centers contains a tetrahydropyranyl ring, a divinylcyclopropyl ring, and a dihydropyranyl ring linked to each other via three (E) double bonds. This review is aimed at highlighting the recent progresses in the area, including the biological activity, a comparison of the 4 total syntheses and the original strategies developed for the partial syntheses.

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Section: Hetero-diels-alder Strategymentioning

confidence: 99%

Section: Hetero-diels-alder Strategymentioning

confidence: 99%

Section: Our Group's Partial Synthesismentioning

confidence: 99%

Section: Our Group's Partial Synthesismentioning

confidence: 99%

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An Overview of Synthetic and Biological Studies of Ambruticin and Analogues

Michelet¹,

Genêt

2005

COC

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Dihydropyrans by Cycloadditions of Oxadienes

et al. 2020

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3,4‐Dihydro‐2H‐pyrans are present in the skeletons of several natural products, and these versatile synthetic intermediates are readily transformed into tetrahydropyrans, pyridines, or 1,5‐dicarbonyl units. Among the strategies developed to access 3,4‐dihydro‐2H‐pyrans, the hetero‐Diels‐Alder reaction between an oxadiene and a dienophile is particularly valuable because up to three contiguous stereogenic centers can be created diastereo‐ and/or enantioselectively in a single step. This review addresses the mechanism of the reaction and presents methods for preparing the product dihydropyrans enantio‐ and diastereoselectively. Thermal and Lewis acid promoted cycloadditions are discussed, as is the role of activating groups on the oxadiene.

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