Studies Towards the Synthesis of Medermycin via Dötz Benzannulation

Qu, Chunrong; Tang, E.; Loeppky, Richard N.; Deng, Zixin; Pulley, Shon R.; Hong, Xuechuan

doi:10.1002/chir.22383

Cited by 7 publications

(4 citation statements)

References 25 publications

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“…Scheme 23 Fernandes' synthesis of hemi--actinorhodin (17) and hemiactinorhodin (16) 3.13 Synthesis of the Core Structure of Medermycin (20) 64 Medermycin was first isolated in 1976 by Takano et al 65a from Streptomyces sp. and has a unique -C-glycoside linkage of an aminosugar, D-angolosamine.…”

Section: Account Syn Lettmentioning

confidence: 99%

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A Decade with Dötz Benzannulation in the Synthesis of Natural Products

Fernandes

Kumari²,

Pathare

2020

Synlett

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The Dötz benzannulation is a named reaction that utilizes Fischer chromium carbenes in a formal [3+2+1] cycloaddition with an alkyne and CO to produce the corresponding benzannulated product. Since its development in the 1970s, this reaction has been extensively used in the synthesis of natural products and various molecular architectures. Although the reaction sometimes suffers from the formation of other competing side products, the rapid construction of naphthol structures with a 1,4-dihydroxy unit makes it the most appropriate reaction for the synthesis of p-naphthoquinones. This review focuses on our group’s efforts over the past decade on the extensive use of this annulation reaction along with the contributions of others on the synthesis of different natural products.1 Introduction2 General Description and Mechanism of the Dötz Benzannulation Reaction3 Applications of the Dötz Benzannulation in Natural Product Synthesis over the Last Decade4 Conclusion

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Section: Account Syn Lettmentioning

confidence: 99%

“…It shows prominent activity against Gram-positive bacteria and also inhibits human leukemic K-562 cells and platelet aggregation. 65b Hong and co-workers 64…”

Section: Account Syn Lettmentioning

confidence: 99%

A Decade with Dötz Benzannulation in the Synthesis of Natural Products

Fernandes

Kumari²,

Pathare

2020

Synlett

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“…[15,22] This generates a reactive a-glycosyl tosylate species that interacts with acceptors through an S N 2 process that shows excellent bselectivity. [22,23] Following the reliable glycosylation as described by Bennett and co-workers, [15,22] we prepared the blinked trisaccharide fragments on a gram scale (see the Supporting Information for details).…”

Section: Asymmetric Total Synthesis Of the Complex Polycyclic Xanthonmentioning

confidence: 99%

Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD‐594

et al. 2020

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A highly convergent approach was developed to achieve the first asymmetric and scalable total synthesis of FD‐594, a complex polycyclic xanthone natural product from Streptomyces sp. TA‐0256, in a longest linear sequence (LLS) of 20 steps. The trans‐9,10‐dihydrophenanthrene‐9,10‐diol fragment (B‐C‐D ring) was generated through a new strategy involving asymmetric dihydroxylation followed by Cu‐mediated oxidative cyclization. Late‐stage stereoselective glycosylation assembled the angular hexacyclic framework with a β‐linked 2,6‐dideoxy trisaccharide fragment.

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“…Its strong activity against Gram‐positive bacteria and ability to inhibit human leukaemia K‐562 cells and platelet aggregation made it a prior target for its synthesis. In this context, Hong and co‐worker have utilized the Dötz reaction followed by acetylation of phenolic group for the construction of C ‐arylglycoside by combining the alkyne 287 with vinylic carbene complex 288 to afford the C ‐arylglycoside 290 in 56% yield (two steps) which was then transformed into the desired medermycin 291 after several steps (Scheme ) …”

Section: Synthesis Of Natural Productsmentioning

confidence: 99%

The Dötz Benzannulation Reaction: A Booming Methodology for Natural Product Synthesis

2020

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Since its finding in 1975, the Dötz benzannulation reaction has attracted a great attention of the scientific community as it permits the regio‐controlled construction of functionalised aromatic frameworks from acyclic precursors. In recent years, this beautifully simple yet much powerful technique for the formation of C−C bonds has opened‐up new possibilities in modern synthetic organic chemistry. In this Review, we report the developments in natural products synthesis by employing the Dötz benzannulation as a key transformation. Although, a flow of publications have witnessed a constant progress in this wonderful area of research, but to our best knowledge this is the first review which purely focuses on the applications of the Dötz benzannulation reaction in natural product synthesis. We are assured that this review will act as a promoter in amplifying the applications of the Dötz benzannulation in the domain of synthetic organic chemistry.

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Studies Towards the Synthesis of Medermycin via Dötz Benzannulation

Cited by 7 publications

References 25 publications

A Decade with Dötz Benzannulation in the Synthesis of Natural Products

A Decade with Dötz Benzannulation in the Synthesis of Natural Products

Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD‐594

The Dötz Benzannulation Reaction: A Booming Methodology for Natural Product Synthesis

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