Total Synthesis of Adunctin B

Dethe, Dattatraya H.; Dherange, Balu D.

doi:10.1021/acs.joc.8b00015

Cited by 23 publications

(6 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Arboridinine Kopsia arborea (plant) 5 1 6 2 3 1 6 adunctin B (Dethe and Dherange, 2018) Piper adunctum (plant) 4 1 8 1 3 6 2 3 (±)-deguelin Tephrosia vogelii (plant) 5 1 9 3 2 4 6 2 englerin A (Hatakeyama, 2018) Phyllanthus engleri (plant) 5 1 9 2 6 2 3 1 3 houttuynoid A (Jian et al, 2018) Houttuynia cordata (plant) 5 2 2 3 4 7 2 4 (−)-mucosin (Nolsoe et al, 2018) Reniera mucosa ( This kind of tool would incredibly ease the access to plant natural chemical diversity and should ideally be comprehensive, organized and include data from worldwide plant species, from past to recent studies. Such a globalized database could furthermore be integrated to other ones like genomic, phylogenic, species occurrence, biosynthetic pathway, biological activity, or chemical classification (Allen et al, 2019) allowing researchers to mine the resources and correlate the information, hence empowering all kind of research studies.…”

Section: Discussionmentioning

confidence: 99%

Unraveling Plant Natural Chemical Diversity for Drug Discovery Purposes

Lautie

Russo

Ducrot³

2020

Front. Pharmacol.

166

120

View full text Add to dashboard Cite

The screening and testing of extracts against a variety of pharmacological targets in order to benefit from the immense natural chemical diversity is a concern in many laboratories worldwide. And several successes have been recorded in finding new actives in natural products, some of which have become new drugs or new sources of inspiration for drugs. But in view of the vast amount of research on the subject, it is surprising that not more drug candidates were found. In our view, it is fundamental to reflect upon the approaches of such drug discovery programs and the technical processes that are used, along with their inherent difficulties and biases. Based on an extensive survey of recent publications, we discuss the origin and the variety of natural chemical diversity as well as the strategies to having the potential to embrace this diversity. It seemed to us that some of the difficulties of the area could be related with the technical approaches that are used, so the present review begins with synthetizing some of the more used discovery strategies, exemplifying some key points, in order to address some of their limitations. It appears that one of the challenges of natural product-based drug discovery programs should be an easier access to renewable sources of plant-derived products. Maximizing the use of the data together with the exploration of chemical diversity while working on reasonable supply of natural product-based entities could be a way to answer this challenge. We suggested alternative ways to access and explore part of this chemical diversity with in vitro cultures. We also reinforced how important it was organizing and making available this worldwide knowledge in an "inventory" of natural products and their sources. And finally, we focused on strategies based on synthetic biology and syntheses that allow reaching industrial scale supply. Approaches based on the opportunities lying in untapped natural plant chemical diversity are also considered.

show abstract

Section: Discussionmentioning

confidence: 99%

Unraveling Plant Natural Chemical Diversity for Drug Discovery Purposes

Lautie

Russo

Ducrot³

2020

Front. Pharmacol.

166

120

View full text Add to dashboard Cite

show abstract

“…Hydrolysis of the acetate and cyclization with K 2 CO 3 in MeOH at room temperature for 40 min afforded tetracyclic tertiary alcohol 30 . We tested different conditions (Burgess reagent, 24 Martin reagent 25 ) for the dehydration of compound 30 and found that in the presence of SOCl 2 and DMAP at −40 °C, exocyclic alkene 31 exhibited complete regioselectivity. 26 Exocyclic alkene 31 was subjected to one-pot dihydroxylation/oxidative cleavage and subsequent reductive deoxygenation in the presence of zinc and sodium( i ) acetate yielded 35% alkenyl ketone 32 27 which produced NMR and high-resolution mass spectrometric results identical to those previously reported by Parker's group.…”

Section: Resultsmentioning

confidence: 99%

Bio-inspired formal total synthesis of (±)-bisabosqual A

Liu

et al. 2023

Org. Chem. Front.

View full text Add to dashboard Cite

show abstract

“…Interestingly, in the total synthesis of (±)‐adunctin B ( 145 ), a natural product isolated from Piper aduncum (Piperaceae), achieved by the same two authors, compound 141 , bearing two free OH groups, could not be directly converted to 144 by a one‐pot epoxidation/EPC, because of either decomposition of 141 or no reaction (Scheme 33). [46] Therefore, double O ‐acetylation of 141 was carried out to make the benzene ring less electron rich and the resulting product 142 was epoxidized by m ‐CPBA to obtain 143 as a single diastereomer. A subsequent one‐pot double deacetylation/5‐ exo EPC successfully delivered tricyclic intermediate 144 which was then advanced to the target natural product 145 over two steps.…”

Section: Construction Of Benzo‐fused Heterocycles By Epoxide–o‐nucleo...mentioning

confidence: 99%

Construction of Benzo‐Fused Heterocycles by Epoxide–Heteronucleophile Cyclization: Applications in the Synthesis of Natural Products and Designed Molecules

Das

2022

Eur J Org Chem

View full text Add to dashboard Cite

Construction of benzo‐fused heterocycles, specifically which have one or more sp3 stereogenic carbon atoms on the heterocyclic ring, by intramolecular ring‐opening cyclization of epoxides with O‐ and N‐nucleophiles is a powerful synthetic tool in organic synthesis. In this Review, we analyze the efficiency of such a heterocyclization approach in natural product synthesis and synthetic methodologies published since the year 2000. In addition to briefly discussing the synthetic methods of accessing the requisite epoxide substrates, important aspects of the subsequent cyclization reaction, such as reaction conditions, endo‐ versus exo‐regioselectivity, protecting or functional group compatibility, and enantio‐ and distereoselectivity are surveyed. Although the literature of organic chemistry in the last four decades has witnessed a large number of reviews/book chapters on the epoxide ring‐opening chemistry, the title topic has never been reviewed. Herein, we have systematized it as a dedicated review for the first time.

show abstract

Total Synthesis of Adunctin B

Cited by 23 publications

References 15 publications

Unraveling Plant Natural Chemical Diversity for Drug Discovery Purposes

Unraveling Plant Natural Chemical Diversity for Drug Discovery Purposes

Bio-inspired formal total synthesis of (±)-bisabosqual A

Construction of Benzo‐Fused Heterocycles by Epoxide–Heteronucleophile Cyclization: Applications in the Synthesis of Natural Products and Designed Molecules

Contact Info

Product

Resources

About