Total Synthesis of the Proposed Structure of (±)-Nidemone

Hsu, Day‐Shin; Yeh, Jen-Yu; Cheng, Chiao-Yun

doi:10.1021/acs.orglett.7b02645

Cited by 10 publications

(6 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Total synthesis of the suggested structure of (±)‐nidemone 257 has been performed either from 2‐hydroxy‐6‐MeO‐benzaldehyde 253 or 2‐Br‐6‐MeO‐benzaldehyde 255 in 10 and 13 synthetic steps, respectively. Noticeably, Sonogashira coupling, regioselective hydrogenation, and also an intramolecular Stetter reaction were considered as the key steps in this approach [121] …”

Section: Application Of Stetter Reaction In Total Synthesis Of Natura...mentioning

confidence: 99%

“…[121] Hsu et al in 2017 achieved and reported two different methods for the formation of enone-benzaldehyde 254 from 2hydroxy-6-methoxybenzaldehyde 253 and 2-bromo-6-methoxybenzaldehyde 255 in three and six synthetic steps, respectively. [121] However, the three-step reaction affords a lower total yield (nearly 34% yield) in comparison with the six step reaction (55% yield). In the following, spirocyclic 1,4-dione 256 provided from the key intermediate 254 through an intramolecular Stetter reaction.…”

Section: Application Of Stetter Reaction In Total Synthesis Of Natura...mentioning

confidence: 99%

“…Upon six steps, (�)-nidemone 257 was synthesized from 256 successfully (Scheme 61). [121] The revised structure of (�)-nidemone 261 was synthesized from 6-bromo-2-hydroxybenzaldehyde 258. Worthy to mention that, in this approach, the key steps are Sonogashira coupling, regioselective hydrogenation, and also an intramolecular Stetter reaction.…”

Section: Application Of Stetter Reaction In Total Synthesis Of Natura...mentioning

confidence: 99%

See 2 more Smart Citations

Recent Advances in Stetter Reaction and Related Chemistry: An update

et al. 2020

View full text Add to dashboard Cite

The Stetter reaction is actually a special CÀ C bond forming reaction through a 1,4-addition reaction in the presence of nucleophilic catalyst. It involves a reaction between aldehydes and Michael acceptors catalyzed by Nheterocyclic carbenes (NHC's) leading to preparation of 1,4dicarbonyl compounds via carbon-carbon bond formation. It offers a powerful approach to access 1,4-dicarbonyl compounds which are significant starting materials and inter-mediates in the synthesis of several heterocyclic systems, and bioactive heterocyclic framework which are present in natural products. In this review we try to underscore the recent advances in Stetter reaction and its applications from 2015 till date. Notably, we focused on the applications of Stetter reaction in the synthesis of various heterocyclic systems and total synthesis of natural products, which have largely been overlooked, previously.

show abstract

Section: Application Of Stetter Reaction In Total Synthesis Of Natura...mentioning

confidence: 99%

Section: Application Of Stetter Reaction In Total Synthesis Of Natura...mentioning

confidence: 99%

Section: Application Of Stetter Reaction In Total Synthesis Of Natura...mentioning

confidence: 99%

See 1 more Smart Citation

Recent Advances in Stetter Reaction and Related Chemistry: An update

et al. 2020

View full text Add to dashboard Cite

show abstract

“…In addition, various biologically active spirocycles including chiral ligands 237 , which shows selectivity and affinity towards bulged RNA structures and AZD3293 ( 238 ) is a β‐secretase‐1 inhibitor . Recently, Hsu and co‐workers disclosed the first total synthesis of (±)‐nidemone ( 239 ), possess spiro linkage as a structural element which exhibit the interesting biological activities . A new type of spirocyclic derivative, pestaloficin A ( 240 ) was reported by Yin and co‐workers .…”

Section: Spirocyclesmentioning

confidence: 99%

“…[61] Recently, Hsu and co-workers disclosed the first total synthesis of (AE)nidemone (239), possess spiro linkage as a structural element which exhibit the interesting biological activities. [62] A new type of spirocyclic derivative, pestaloficin A (240) was reported by Yin and co-workers. [63] Spiroreticulatine (241) is a spiro quinoline-imidazole alkaloid derived from sponge, which exhibit inhibitory activity on IL-2 production.…”

Section: Spirocyclesmentioning

confidence: 99%

Design and Synthesis of Polycycles, Heterocycles, and Macrocycles via Strategic Utilization of Ring‐Closing Metathesis

Kotha

Meshram

Dommaraju

2018

The Chemical Record

View full text Add to dashboard Cite

In this perspective, we summarize new synthetic approaches for the construction of various polycyclic compounds involving ring-closing metathesis as a key step. In this regard, we used ring-closing metathesis in combination with other popular reactions like Suzuki-Miyaura coupling, Claisen rearrangement, Fischer indolization, Grignard addition, Diels-Alder reaction, and [2+2] cycloaddition reaction etc. To this end, a variety of functional molecules such as α-amino acids, cyclophanes, heterocycles, propellanes, spirocycles, and macrocycles have been prepared. The strategies developed and the molecules prepared here play a key role in designing new materials and also act as lead compounds in drug design. The strategies and tactics developed here are useful to design polycycles, macrocycles, and heterocycles of diverse ring systems.

show abstract

The Catalytic Enantioselective Stetter Reaction

Flanigan¹,

Ozboya²,

Tanpure³

et al. 2021

Organic Reactions

View full text Add to dashboard Cite

The catalytic enantioselective Stetter reaction is the coupling of an aldehyde with an electron‐deficient alkene via the conjugate addition of an acyl anion equivalent (Breslow intermediate) generated from the aldehyde and a chiral N ‐heterocyclic carbene (NHC) catalyst. The process affords 1,4‐dicarbonyl compounds and related systems, such as β‐nitroketones, in an efficient and atom‐economical fashion and with generally good‐to‐excellent enantioselectivities when fused polycyclic chiral triazolylidenes are employed as the NHC catalysts. The scope of the transformation is particularly broad for intramolecular reactions, but in the case of the intermolecular variant, only certain types of aldehyde donors and electrophilic alkenes can be successfully coupled together. This chapter describes theoretical and operational aspects of the catalytic enantioselective Stetter reaction such that the reader will be able to obtain optimal results in their own research. A detailed mechanistic overview is included to account for the factors that influence stereoselectivity and yield, and results from experimental and computational mechanistic studies are summarized. In addition, catalyst synthesis, reaction variants, applications in target‐directed synthesis, and comparison to other methods for generating 1,4‐dicarbonyl compounds are also presented. Tabular surveys are organized according to the modality of reactivity, either intra‐ or intermolecular, and the type of aldehyde donor. The literature is covered from the first disclosure of a catalytic enantioselective Stetter reaction in 1996 through to the end of 2019.

show abstract

Total Synthesis of the Proposed Structure of (±)-Nidemone

Cited by 10 publications

References 21 publications

Recent Advances in Stetter Reaction and Related Chemistry: An update

Recent Advances in Stetter Reaction and Related Chemistry: An update

Design and Synthesis of Polycycles, Heterocycles, and Macrocycles via Strategic Utilization of Ring‐Closing Metathesis

The Catalytic Enantioselective Stetter Reaction

Contact Info

Product

Resources

About