A general strategy for diverse syntheses of anhydrolandomycinone, tetrangulol, and landomycinone

Sie, Cheng-Jhe; Patteti, Venukumar; Yang, Yun-Liang; Mong, Kwok-Kong Tony

doi:10.1039/c7cc09818a

Cited by 9 publications

(5 citation statements)

References 34 publications

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“…Currently available protocols toward their aglycone core structure and glycone component alone are inadequate for procurement of a complete LA scaffold. 20,21 Some modifications are required for selective removal of protecting groups and subsequent coupling reactions; but such modifications may not be tolerable to the original protocols. Thereby, we envisaged some synthetic challenges to realize the structures of our targets.…”

Section: Resultsmentioning

confidence: 99%

Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties

Lai

Mondal

et al. 2021

RSC Adv.

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Section: Resultsmentioning

confidence: 99%

Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties

Lai

Mondal

et al. 2021

RSC Adv.

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“…Landomycins, with potent antiproliferation and antibiotic activities, 70 consist of an angular tetracyclic unit fused with a deoxyoligosaccharide framework and were isolated from Streptomyces bacteria. 71 Mong et al 69 3.16 Synthesis of (-)-Juglomycin C (18a) and (-)-NHAB (18b) 72 We recently completed step-economic and efficient syntheses of (S)-(-)-juglomycin C (18a) and (S)-(-)-NHAB (18b) employing the Dötz benzannulation reaction (Scheme 28). 72 The former was isolated from Streptomyces sp.…”

Section: Total Syntheses Of Anhydrolandomycinone (21) Landomycinone (22) and Tetrangulol (23) 69mentioning

confidence: 99%

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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“…Recently, Mong and co‐worker reported the total synthesis of tetrangulol through the Dötz benzannulation between Fischer carbene complex 352 and alkyne 353 to provide the annulated product naphthalene‐1‐ol ( 354) which was then subjected to demethylation followed by reduction and Cbz‐protection to deliver the compound 355 . Finally, the compound 355 gave the desired natural product after several steps as depicted in the 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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A general strategy for diverse syntheses of anhydrolandomycinone, tetrangulol, and landomycinone

Abstract: A general synthetic strategy based on a protecting group-promoted CH arylation method was developed for total syntheses of anhydrolandomycinone (1), tetrangulol (2), and landomycinone (3) from the same set of starting materials.

Cited by 9 publications

References 34 publications

Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties

Total synthesis of landomycins Q and R and related core structures for exploration of the cytotoxicity and antibacterial properties

A Decade with Dötz Benzannulation in the Synthesis of Natural Products

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

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