2013
DOI: 10.1080/00397911.2011.624395
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Concise Stereoselective Total Synthesis of (+)-Mueggelone

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Cited by 10 publications
(5 citation statements)
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“…First, aldehyde 6 was prepared from commercially available cis -hex-3-en-1-ol in several steps, including a Katsuki-Sharpless asymmetric epoxidation reaction (Supporting Information). 15 The absolute configuration set in the epoxidation process was assured via correlation with previously reported data. 16 An E -selective Wittig reaction 17 between 6 and the commercially available ylide (triphenylphosphoranylidene)acetaldehyde ( 7 ) furnished stereochemically pure aldehyde 8 in 61% yield after chromatographic purification.…”
Section: Resultsmentioning
confidence: 99%
“…First, aldehyde 6 was prepared from commercially available cis -hex-3-en-1-ol in several steps, including a Katsuki-Sharpless asymmetric epoxidation reaction (Supporting Information). 15 The absolute configuration set in the epoxidation process was assured via correlation with previously reported data. 16 An E -selective Wittig reaction 17 between 6 and the commercially available ylide (triphenylphosphoranylidene)acetaldehyde ( 7 ) furnished stereochemically pure aldehyde 8 in 61% yield after chromatographic purification.…”
Section: Resultsmentioning
confidence: 99%
“…

Chiral allylic alcohols of w-alkenoic acids and derivatives thereof are highly important building blocks for the synthesis of biologically active compounds. [2] A chemoenzymatic route with an alcohol dehydrogenase catalyzed selective reduction as the key step was reported by our group and represents arguably the most efficient access nowadays (2 or 3 steps, 73-77 % overall yield, > 99 % ee, both enantiomers accessible). Described herein is an enzymatic approach using the P450 BM3 monooxygenase mutant A74G/L188Q, which catalyzes allylic hydroxylation with high to excellent chemo-and enantioselectivities providing the desirable secondary alcohols.

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mentioning
confidence: 99%
“…[1] Extensive research toward the enantioselective synthesis of these moieties has resulted in multistep approaches comprising prefunctionalization and protection group chemistry as well as functional group interconversions and oxidation state manipulations. [2] A chemoenzymatic route with an alcohol dehydrogenase catalyzed selective reduction as the key step was reported by our group and represents arguably the most efficient access nowadays (2 or 3 steps, 73-77 % overall yield, > 99 % ee, both enantiomers accessible). [3] Significant streamlining could be achieved by the direct asymmetric oxidation of readily available "unactivated" olefins at the allylic position, providing a highly atom-economic single-step process.…”
mentioning
confidence: 99%
“…The methyl ester of 16 S ,17 S -ePD n-3 DPA was constructed via two key precursors ( Figure 3 A). These precursors were obtained using the following stereoselective reactions: a Katsuki-Sharpless epoxidation protocol ( Kumar and Meshram, 2013 ) and one Z - and two E -selective Wittig reactions ( Maryanoff and Reitz, 1989 ). The detailed description of the synthetic route is reported in Primdahl et al.…”
Section: Resultsmentioning
confidence: 99%