An AC → ABC approach to taxol involving B-ring closure at C-1–C-2

Swindell, Charles S.; Chander, Madhavi C.; Heerding, Julia M.; Klimko, Peter G.; Rahman, Leera T.; Raman, Jaishree; Vencataraman, Hemalatha

doi:10.1016/s0040-4039(00)61582-4

Cited by 18 publications

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“…Reductive cyclization of a keto aldehyde precursor (cf. 48 ) was of particular interest because it offered the prospect of delivering the C 1 −C 2 functionality, configured in its required sense (see 49 ) . We achieved the coupling of lithium reagent 34 with several relevant aldehydes.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Baccatin III and Taxol

et al. 1996

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An intramolecular Heck reaction (90 f 91) serves as the key step in the total synthesis of the titled compounds. The synthetic route is based on utilizing the Wieland-Miescher ketone (5) as a matrix to provide the C and D rings of the targets and to provide functionality implements for joining this sector to an A ring precursor (6). Catalytically induced enantiotopic control and early emplacement of the oxetane are other features of the route.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of Baccatin III and Taxol

et al. 1996

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“…An unidentified contaminant accompanied the 12 so produced, but it proved convenient to convert unpurified 12 to 14 through intermediate keto aldehyde 13 , probably because alternative keto aldehyde byproducts fail to undergo efficient pinacol cyclization. When the pinacol coupling step was carried out with pure 13 , 14 was formed in 86% yield 14a. The sequence illustrated in Scheme provides 14 in ten linear steps from commercially available materials.…”

Section: Resultsmentioning

confidence: 99%

Taxane Synthesis through Intramolecular Pinacol Coupling at C-1−C-2. Construction and Oxidative Transformations of a C-Aromatic Taxane Diene

et al. 1996

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A ten-linear-step construction of C-aromatic taxane diene 14 from ethyl isopropyl ketone, acryloyl chloride, and commercially available 8 is reported. This sequence concludes with an intramolecular pinacol coupling carried out on 13. 14 is oxidized by m-chloroperbenzoic acid and dimethyldioxirane to give 17 through intermediate epoxide 20 and by VO(acac)2−t-BuOOH and Mo(CO)6−t-BuOOH to give 13. 17 is converted efficiently into 22 upon treatment with Mo(CO)6−t-BuOOH, apparently through an unusual equilibration with isomeric 20, which is converted irreversibly to 22. While these oxidative transformations highlight some of the peculiar reactivity patterns characteristic of taxane-related structures, the formation of 14 through an intramolecular pinacol coupling that joins C-1 and C-2 demonstrates the potential of this strategy for stereoselectively delivering advanced taxane synthesis intermediates.

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