Total Syntheses of Festuclavine, Pyroclavine, Costaclavine, <i>epi</i>-Costaclavine, Pibocin A, 9-Deacetoxyfumigaclavine C, Fumigaclavine G, and Dihydrosetoclavine

Liu, Haichao; Zhang, Xiwu; Shan, Dong; Pitchakuntla, Mallesham; Ma, Yongfan; Jia, Yanxing

doi:10.1021/acs.orglett.7b01504

Cited by 41 publications

(28 citation statements)

References 69 publications

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“…The cyclization is terminated by a TMSdirected Heck reaction, and the TMS group can also be removed in one-pot in a high ratio, resulting in an exocyclic double bond for further transformation (Figure 6A). In the same year, Jia's group (Liu et al, 2017) accomplished a collective total synthesis of eight ergot alkaloids, in which a new cascade reaction was developed for one-pot assembly of the common B/C/D rings in the tetracyclic ergot scaffold (Figure 6B). This reaction involves an intramolecular Larock indole annulation and a Tsuji-Trost allylation, which are both catalyzed by palladium and can be integrated in one pot.…”

Section: Construction Of Polycyclic Heterocycles Fused Pyridines and mentioning

confidence: 99%

Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation

Zheng

Hua

2020

Front. Chem.

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Polycyclic scaffolds are omnipresent in natural products and drugs, and the synthetic strategies and methods toward construction of these scaffolds are of particular importance. Compared to simple cyclic ring systems, polycyclic scaffolds have higher structure complexity and diversity, making them suitable for charting broader chemical space, yet bringing challenges for the syntheses. In this review, we surveyed progress in the past decade on synthetic methods for polycyclic natural product scaffolds, in which the key steps are one-pot reactions involving intermolecular or intramolecular alkyne annulation. Synthetic strategies of selected polycyclic carbocycles and heterocycles with at least three fused, bridged, or spiro rings are discussed with emphasis on the synthetic efficiency and product diversity. Recent examples containing newly developed synthetic concepts or toolkits such as collective and divergent total synthesis, gold catalysis, C-H functionalization, and dearomative cyclization are highlighted. Finally, several "privileged synthetic strategies" for "privileged polycyclic scaffolds" are summarized, with discussion of remained challenges and future perspectives.

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Section: Construction Of Polycyclic Heterocycles Fused Pyridines and mentioning

confidence: 99%

Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation

Zheng

Hua

2020

Front. Chem.

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“…As shown in Scheme , densely functionalized ortho‐ bromoaniline derivative 44 was treated with 20 mol% of Pd(OAc) 2 and 40 mol% of Me‐phos to give the corresponding product 45 in 92% yield. Compound 45 was successfully applied to the divergent total synthesis of eight kinds of ergot alkaloids …”

Section: Synthesis Of 34‐fused Tricyclic Indoles Via a Direct Formatmentioning

confidence: 99%

Synthetic Methods for 3,4‐Fused Tricyclic Indoles via Indole Ring Formation

2018

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3,4-Fused tricyclic indole frameworks are found in various bioactive natural products and pharmaceuticals. The development of an efficient synthetic method for this structural motif has therefore attracted attention in the field of synthetic organic chemistry and medicinal chemistry. Herein, we summarize recent advances in the synthesis of 3,4-fused tricyclic indoles. This class of synthetic methods can be roughly classified into two categories: methods using functionalized indole derivatives as starting materials to construct a fused medium-sized ring (Types A-D: Category I), and methods of constructing a 3,4-fused tricyclic indole skeleton via indole ring formation (Types E-G: Category II). In this focus review, synthetic methods for 3,4-fused tricyclic indoles classified as Category II methods are highlighted, following a brief overview of the Category I methods. 2 3 4 5 6 7 8

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“…In 2017, Jia and co-workers reported the efficient construction of the ergot alkaloid core through a palladiumcatalyzed tricyclization (Scheme 4). 15 Their strategy was based on the Larock indole formation, which proceeds through oxidative addition of bromoaniline derivative 22 to Pd(0), carbopalladation onto the alkyne, and nucleophilic attack by an amino group. Substrate 22 was prepared in seven steps from allylic bromide 20, dibromide 21, and optically active tert-butylsulfinamide.…”

Section: Termination With Nitrogen Nucleophilesmentioning

confidence: 99%

Recent Progress in Palladium-Catalyzed Cascade Cyclizations for Natural Product Synthesis

Ohno

Inuki

2018

Synthesis

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Cascade reactions (also represented as domino reactions) realize the step-economical direct construction of natural product core structures. The use of atom-economical elementary reactions in cascade processes can minimize waste production and avoid prefunctionalization of the substrates. Palladium catalysis, which promotes a variety of atom-economical elementary reactions, has long been used as a powerful approach to the direct formation of complex heterocycles. In this short review, palladium-catalyzed cascade reactions for the construction of core structures of natural products reported in the last decade are highlighted.1 Introduction2 Reactions Terminated with Heteronucleophiles2.1 Termination with Nitrogen Nucleophiles2.2 Termination with Oxygen Nucleophiles3 Reactions Terminated with Carbon Functional Groups3.1 Termination with Carbon Nucleophiles3.2 Termination with Heck-Type Reactions4 Conclusion

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Total Syntheses of Festuclavine, Pyroclavine, Costaclavine, epi-Costaclavine, Pibocin A, 9-Deacetoxyfumigaclavine C, Fumigaclavine G, and Dihydrosetoclavine

Cited by 41 publications

References 69 publications

Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation

Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation

Synthetic Methods for 3,4‐Fused Tricyclic Indoles via Indole Ring Formation

Recent Progress in Palladium-Catalyzed Cascade Cyclizations for Natural Product Synthesis

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