Benzoate dioxygenase from<i>Ralstonia eutropha</i>B9 – unusual regiochemistry of dihydroxylation permits rapid access to novel chirons

Griffen, Julia A.; Kenwright, Sarah J.; Abou‐Shehada, Sarah; Wharry, Scott; Moody, Thomas S.; Lewis, Simon E.

doi:10.1039/c3qo00057e

Cited by 19 publications

(9 citation statements)

References 162 publications

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“…Therefore, this is an efficient approach to the synthesis of syn -1,2:3,4-diepoxides from 1,3-dienes under mild conditions. Table 30 summarizes the results of the cobalt(II) tetraphenylporpyrin-catalyzed rearrangement of endoperoxides 576 [ 509 ], 578 [ 510 ], 580 [ 511 ], 582 [ 512 ], 584 [ 353 ], 586 [ 513 ], 588 [ 514 ], 590 , 592 [ 515 ], 594 [ 516 ], 596 [ 517 ], and 598 [ 518 ] which afforded products structurally similar to the diepoxides prepared by thermal rearrangement of endoperoxides ( Table 25 ). All rearrangements were stereospecific and yielded only the syn -diepoxides.…”

Section: Reviewmentioning

confidence: 99%

Rearrangements of organic peroxides and related processes

Yaremenko¹,

Vil²,

Demchuk³

et al. 2016

Beilstein J. Org. Chem.

195

136

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SummaryThis review is the first to collate and summarize main data on named and unnamed rearrangement reactions of peroxides. It should be noted, that in the chemistry of peroxides two types of processes are considered under the term rearrangements. These are conventional rearrangements occurring with the retention of the molecular weight and transformations of one of the peroxide moieties after O–O-bond cleavage. Detailed information about the Baeyer−Villiger, Criegee, Hock, Kornblum−DeLaMare, Dakin, Elbs, Schenck, Smith, Wieland, and Story reactions is given. Unnamed rearrangements of organic peroxides and related processes are also analyzed. The rearrangements and related processes of important natural and synthetic peroxides are discussed separately.

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Section: Reviewmentioning

confidence: 99%

Rearrangements of organic peroxides and related processes

Yaremenko¹,

Vil²,

Demchuk³

et al. 2016

Beilstein J. Org. Chem.

195

136

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“…Functionalization of the primary alcohol 5 with benzoyl chloride afforded benzoate 6 in 82 % yield and with high selectivity. A similar strategy has been recently reported by Lewis and co‐workers for the synthesis of functionalized cyclohexyl chiron derivatives of diol 2 10. Compound 6 was then submitted to Upjohn dihydroxylation conditions to obtain cis ‐diol 7 in 78 % yield after chromatographic purification.…”

Section: Resultsmentioning

confidence: 94%

First Total Synthesis of Piperenol B and Configuration Revision of the Enantiomers Piperenol B and Uvarirufol A

et al. 2015

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We report herein the first total synthesis of piperenol B, a polyoxygenated cyclohexene derivative with reported pharmacological activity isolated from Piper cubeb. The chiral building block for this synthetic approach is derived from microbial cis‐ipso,ortho‐dihydroxylation of sodium benzoate, which was optimized to the multi‐ten‐gram scale by reaction medium engineering. Final‐stage deprotection of an acetonide was investigated in detail, leading to an efficient eight‐step protocol for the synthesis of piperenol B with a total yield of 10 %. Most importantly, the previously assigned absolute configuration of piperenol B was revised and unequivocally established by 2D NMR analysis and the Mosher's ester method.

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“…143-146 ( Figure 6). 36 This report also details routes to C-hydroxymethyl-mucoinositol 147 and bis(epoxide) 148.…”

Section: Scheme 14 Total Synthesis Of (-)-Idesolide By Hudlický and mentioning

confidence: 96%

Applications of biocatalytic arene ipso,ortho cis-dihydroxylation in synthesis

Lewis

2014

Chem. Commun.

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The dearomatising dihydroxylation of aromatic molecules mediated by arene dioxygenase enzymes can provide cyclohexadiene-diols that are versatile starting materials for organic synthesis. Whereas oxidation of a substituted arene to give its ortho,meta-dihydrodiol has been demonstrated for numerous substrates and dioxygenases, formation of ipso,ortho-dihydrodiols has historically been underutilised in comparison. This feature article presents a chronological account of reported uses of such diols.

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Benzoate dioxygenase fromRalstonia eutrophaB9 – unusual regiochemistry of dihydroxylation permits rapid access to novel chirons

Abstract: Oxidation of benzoic acid by a microorganism expressing benzoate dioxygenase leads to the formation of an unusualipso,orthoarenecis-diol in sufficient quantities to be useful for synthesis.

Cited by 19 publications

References 162 publications

Rearrangements of organic peroxides and related processes

Rearrangements of organic peroxides and related processes

First Total Synthesis of Piperenol B and Configuration Revision of the Enantiomers Piperenol B and Uvarirufol A

Applications of biocatalytic arene ipso,ortho cis-dihydroxylation in synthesis

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