General Synthetic Approach to Functionalized Dihydrooxepines

Nicolaou, K. C.; Yu, Ruocheng; Shi, Lei; Cai, Quan; Lü, Min; Heretsch, Philipp

doi:10.1021/ol4006689

Cited by 33 publications

(20 citation statements)

References 26 publications

(24 reference statements)

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“…A regioselective Baeyer–Villiger oxidation of functionalized cyclohexenones 78 lead to dihydrooxepine structures 79 . Here, the combination of SnCl 4 and bis(trimethylsilyl)peroxide (BTSP), in the presence of trans -1,2-diaminocyclohexane as the ligand, generated the desired products 79 in high yields ( Scheme 25 ) [ 255 ].…”

Section: Reviewmentioning

confidence: 99%

Rearrangements of organic peroxides and related processes

Yaremenko¹,

Vil²,

Demchuk³

et al. 2016

Beilstein J. Org. Chem.

183

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.

183

136

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“…After the preparation of enone 40 , we attempted to convert it into bis(diene) 50 by means of deprotonation and trapping of the kinetic enolate with Comins’ reagent36a or (RO) 2 P(O)Cl36b,c followed by reductive defunctionalization. Several bases such as LDA, LiHMDS, NaHMDS, and KHMDS with and without solvent additives, such as HMPA or DMPU, were examined, but none of the conditions successfully gave 45 .…”

Section: Resultsmentioning

confidence: 99%

A Unified Strategy to 6–5–6–5–6‐Membered Epipolythiodiketopiperazines: Studies towards the Total Synthesis of Scabrosin Diacetate and Haematocin

Zipfel

Carreira

2015

Chemistry A European J

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The family of epipolythiodiketopiperazine (ETP) natural products consists of over 200 members possessing a wide diversity of structures and biological activity. Recently, the subgroup of 6-5-6-5-6-membered ETPs has gained substantial attention, which has resulted in several total syntheses. Despite all the efforts that have been invested into accessing these complex structures, no synthesis of scabrosin diacetate (1 a) and its related esters has been reported. Herein, our attempts towards scabrosin diacetate (1 a) and haematocin (3) starting from diketopiperazine 12 a as a late-stage intermediate are presented. Diketopiperazine 12 a can be conveniently accessed in multigram quantities from aldehyde 18 and diketopiperazine 21 and was envisioned to serve as a general platform for the synthesis of 6-5-6-5-6-membered ETPs.

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“…The same palladium catalyst is very useful to lead an ester group, after the replacement of the phosphate group, with a 52 % yield (product 164). [61] In summary, this minireview has covered the different methodologies developed during the past two decades. A wide range of methods have been developed to gain access to seven membered ring oxacycles (saturated and unsaturated).…”

Section: Ring Expansions Of Cyclohexanonementioning

confidence: 99%

Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches

et al. 2020

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This minireview focuses on recent advances in the synthesis of seven-membered ring oxacycles, whether saturated, unsaturated, fused or isolated. We cover a remarkable variety of strategies and methods developed during the past two decades, based mainly on cyclizations, ring-closing metathesis, conjugate additions, and ring expansions. The cyclizations can be generated directly or triggered through an oxocarbenium ion, carbocation or iminium-type species. Also discussed [a] Prof.

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General Synthetic Approach to Functionalized Dihydrooxepines

Abstract: A three-step sequence to access functionalized 4,5-dihydrooxepines from cyclohexenones has been developed. This approach features a regioselective Baeyer–Villiger oxidation and subsequent functionalization via the corresponding enol phosphate intermediate.

Cited by 33 publications

References 26 publications

Rearrangements of organic peroxides and related processes

Rearrangements of organic peroxides and related processes

A Unified Strategy to 6–5–6–5–6‐Membered Epipolythiodiketopiperazines: Studies towards the Total Synthesis of Scabrosin Diacetate and Haematocin

Synthesis of Seven Membered Oxacycles: Recent Developments and New Approaches

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