A Second-Generation Synthesis of the Cyanthiwigin Natural Product Core

Kim, Kelly E.; Stoltz, Brian M.

doi:10.1021/acs.orglett.6b02962

Cited by 23 publications

(13 citation statements)

References 25 publications

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“…In 2016 the same group improved the synthetic pathway, using an anti-Markovnikov Wacker oxidation, to obtain ketoaldehyde 51 in better yield. 43 In this total synthesis, the double stereoablative decarboxylative allylation provided a chiral building block with high enantiopurity illustrating the power of the amplified process. This example presents also one of the rare use of a centrosymmetric meso compound in total synthesis.…”

Section: Scheme 21 Palladium-catalyzed Double Stereoablative Enantiosmentioning

confidence: 91%

Catalytic Enantioselective Desymmetrization of Meso Compounds in Total Synthesis of Natural Products: Towards an Economy of Chiral Reagents

Merad¹,

Candy²,

Pons³

et al. 2017

Synthesis

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Meso compounds represent a particular family of achiral molecules bearing elements of chirality. Their desymmetrization through enantioselective catalytic methods usually leads to elaborate chiral building blocks containing several stereogenic elements, which can be a very useful and elegant approach in the context of total synthesis. In the present review, the power of this strategy is illustrated through the different possibilities of catalytic enantioselective desymmetrization. From the combination of the hidden symmetry detection and the catalytic enantioselective transformations a new type of economy emerges: the economy of chiral reagents. Conclusion

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Section: Scheme 21 Palladium-catalyzed Double Stereoablative Enantiosmentioning

confidence: 91%

Catalytic Enantioselective Desymmetrization of Meso Compounds in Total Synthesis of Natural Products: Towards an Economy of Chiral Reagents

Merad¹,

Candy²,

Pons³

et al. 2017

Synthesis

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“…This problem was improved significantly in their subsequent report wherein the enantioselective alkylation was carried out on a 10 g scale furnishing the desired diketone ( R , R )- 21-A in 94% yield, 4.2:1 dr and 99% ee . 12 …”

Section: Mono(oxazoline) Ligandsmentioning

confidence: 99%

Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

et al. 2021

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The chiral oxazoline motif is present in many ligands that have been extensively applied in a series of important metal-catalyzed enantioselective reactions. This Review aims to provide a comprehensive overview of the most significant applications of oxazoline-containing ligands reported in the literature starting from 2009 until the end of 2018. The ligands are classified not by the reaction to which their metal complexes have been applied but by the nature of the denticity, chirality, and donor atoms involved. As a result, the continued development of ligand architectural design from mono(oxazolines), to bis(oxazolines), to tris(oxazolines) and tetra(oxazolines) and variations thereof can be more easily monitored by the reader. In addition, the key transition states of selected asymmetric transformations will be given to illustrate the features that give rise to high levels of asymmetric induction. As a further aid to the reader, we summarize the majority of schemes with representative examples that highlight the variation in % yields and % ee s for carefully selected substrates. This Review should be of particular interest to the experts in the field but also serve as a useful starting point to new researchers in this area. It is hoped that this Review will stimulate both the development/design of new ligands and their applications in novel metal-catalyzed asymmetric transformations.

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“…The cyathane structure is different from the homoverrucosane, mulinane, and valparane diterpenoids which also possess a 5/6/7 tricarbocyclic system [ 48 , 49 ]. The cyathanes are most similar to cyanthiwigins and can be differentiated by the orientation of the angular methyl groups, mainly present in some sponges [ 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 ]. These compounds display a diverse range of biological activities, including anticancer, antimicrobial, anti-MRSA (methicillin-resistant Staphylococcus aureus ), anti-inflammatory, anti-proliferative, and nerve growth factor (NGF)-like properties [ 19 , 20 , 60 , 61 ].…”

Section: Cyathanementioning

confidence: 99%

Diterpenes Specially Produced by Fungi: Structures, Biological Activities, and Biosynthesis (2010–2020)

Zhang

Feng

2022

JoF

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Fungi have traditionally been a very rewarding source of biologically active natural products, while diterpenoids from fungi, such as the cyathane-type diterpenoids from Cyathus and Hericium sp., the fusicoccane-type diterpenoids from Fusicoccum and Alternaria sp., the guanacastane-type diterpenoids from Coprinus and Cercospora sp., and the harziene-type diterpenoids from Trichoderma sp., often represent unique carbon skeletons as well as diverse biological functions. The abundances of novel skeletons, biological activities, and biosynthetic pathways present new opportunities for drug discovery, genome mining, and enzymology. In addition, diterpenoids peculiar to fungi also reveal the possibility of differing biological evolution, although they have similar biosynthetic pathways. In this review, we provide an overview about the structures, biological activities, evolution, organic synthesis, and biosynthesis of diterpenoids that have been specially produced by fungi from 2010 to 2020. We hope this review provides timely illumination and beneficial guidance for future research works of scholars who are interested in this area.

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A Second-Generation Synthesis of the Cyanthiwigin Natural Product Core

Cited by 23 publications

References 25 publications

Catalytic Enantioselective Desymmetrization of Meso Compounds in Total Synthesis of Natural Products: Towards an Economy of Chiral Reagents

Catalytic Enantioselective Desymmetrization of Meso Compounds in Total Synthesis of Natural Products: Towards an Economy of Chiral Reagents

Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

Diterpenes Specially Produced by Fungi: Structures, Biological Activities, and Biosynthesis (2010–2020)

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