Asymmetric Total Synthesis of (+)-Didemniserinolipid B via Achmatowicz Rearrangement/Bicycloketalization

Ren, Jingyun; Tong, Rongbiao

doi:10.1021/jo501142q

Cited by 36 publications

(16 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…846 Syntheses of the reported structures of polycitorols A and B (unidentied ascidian) 847,848 and (+)-didemniserinolipid C (Didemnum sp.) 849,850 suggest that the structures of all three MNPs require revision. Total synthesis has also led to revision of the structure of mandelalide A (Lissoclinum sp.)…”

Section: Molluscsmentioning

confidence: 99%

Marine natural products

et al. 2016

View full text Add to dashboard Cite

This review covers the literature published in 2014 for marine natural products (MNPs), with 1116 citations (753 for the period January to December 2014) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1378 in 456 papers for 2014), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

show abstract

Section: Molluscsmentioning

confidence: 99%

Marine natural products

et al. 2016

View full text Add to dashboard Cite

show abstract

“…The oxidation of 2-(trimethylsilyl)furans with mCPBA produces furan-2(3H)-ones. Jia and co-workers used this reaction during their enantioselective synthesis of (-)-pallavicinin (131). They obtained compound 127 starting from furan (126) and then oxidized it with mCPBA to afford unstable furanone 128.…”

Section: Syn Thesismentioning

confidence: 99%

“…Unfortunately, they failed to synthesize this O-sulfate to prove their hypothesis. 131 Tong et al reported the total synthesis of (+)-attenol B starting from furan 345, which was converted into 2-(1,2dihydroxyalkyl)furan 346. Oxidation followed by acidic treatment produced dioxabicyclic compound 347.…”

Section: Scheme 80 Formal Synthesis Of Tirandamycin Bmentioning

confidence: 99%

Furan Oxidation Reactions in the Total Synthesis of Natural Products

2018

View full text Add to dashboard Cite

Recent developments on the transformations of furans under oxidative conditions toward the total synthesis of complex natural compounds are discussed. Reactions and methods are classified according to the type of oxidant used. Comparisons are then made between all the strategies to provide a comprehensive overview. This review covers the most prominent work published from 2011 until 2017.1 Introduction2 Reagents and Methods for Oxidation of the Furan Ring2.1 Singlet Oxygen2.2 Peroxides and Hydroperoxides2.3 Quinones2.4 Halogen-Based Oxidants2.5 Chromium-Based Oxidants3 The Achmatowicz Reaction3.1 Halogen-Based Oxidants3.2 Hydroperoxides3.3 Enzymatic Oxidation4 Conclusion

show abstract

“…104-107 The issues related to the use of bromine and poor water solubility of pyran-3-ones, prompted the development of new non-bromine-based oxidizing agents such as m -CPBA in a variety of solvents. 108-113 This alternative furylcarbinol ring expansion was nicely employed in natural product total syntheses. 114-117 …”

Section: Introductionmentioning

confidence: 99%

“…180 Tong and co-workers utilized an Achmatowicz reaction in the total synthesis of (+)-didemniserinolipid B ( 96 , Scheme 26) in 19 steps from commercially available materials. 108 In particular, the target compound was assembled from the 6,8-DOBCO system ( 97 ). 181-183 The key 6,8-DOBCO fragment 97 was envisioned from hydrogenation and diastereoselective ketone reduction of the bicyclic acetal 98 .…”

Section: Introductionmentioning

confidence: 99%

Achmatowicz reaction and its application in the syntheses of bioactive molecules

Ghosh

Brindisi

2016

RSC Adv.

View full text Add to dashboard Cite

Substituted pyranones and tetrahydropyrans are structural subunits of many bioactive natural products. Considerable efforts are devoted toward the chemical synthesis of these natural products due to their therapeutic potential as well as low natural abundance. These embedded pyranones and tetrahydropyran structural motifs have been the subject of synthetic interest over the years. While there are methods available for the syntheses of these subunits, there are issues related to regio and stereochemical outcomes, as well as versatility and compatibility of reaction conditions and functional group tolerance. The Achmatowicz reaction, an oxidative ring enlargement of furyl alcohol, was developed in the 1970s. The reaction provides a unique entry to a variety of pyranone derivatives from functionalized furanyl alcohols. These pyranones provide convenient access to substituted tetrahydropyran derivatives. This review outlines general approaches to the synthesis of tetrahydropyrans, covering general mechanistic aspects of the Achmatowicz reaction or rearrangement with an overview of the reagents utilized for the Achmatowicz reaction. The review then focuses on the synthesis of functionalized tetrahydropyrans and pyranones and their applications in the synthesis of natural products and medicinal agents.

show abstract

Asymmetric Total Synthesis of (+)-Didemniserinolipid B via Achmatowicz Rearrangement/Bicycloketalization

Cited by 36 publications

References 48 publications

Marine natural products

Marine natural products

Furan Oxidation Reactions in the Total Synthesis of Natural Products

Achmatowicz reaction and its application in the syntheses of bioactive molecules

Contact Info

Product

Resources

About