Total Synthesis of (+)‐Minfiensine: Construction of the Tetracyclic Core Structure by an Asymmetric Cascade Cyclization

Zhang, Ze-Xin; Chen, Sicong; Jiao, Lei

doi:10.1002/anie.201602771

Cited by 54 publications

(23 citation statements)

References 61 publications

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“…This system was also successfully applied to the isomerization of tetracyclic olefin 6 to 7, with the less hindered product 7 isolated in 93% yield, which could be a key step in the total synthesis of (+)-minfiensine (Scheme 7, eq 2). 16…”

Section: Review Syn Thesismentioning

confidence: 99%

Base-Metal-Catalyzed Olefin Isomerization Reactions

Liu

2019

Synthesis

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The catalytic olefin isomerization reaction is a highly efficient and atom-economic transformation in organic synthesis that has attracted tremendous attention both in academia and industry. Recently, the development of Earth-abundant metal catalysts has received growing interest owing to their wide availability, sustainability, and environmentally benign nature, as well as the unique properties of non-precious metals. This review provides an overview of a broad range of base-metal-catalyzed olefin isomerization reactions categorized according to their different reaction mechanisms.1 Introduction2 Base-Metal-Catalyzed Olefin Isomerization Reactions3 Base-Metal-Catalyzed Cycloisomerization Reactions4 Conclusion

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Section: Review Syn Thesismentioning

confidence: 99%

Base-Metal-Catalyzed Olefin Isomerization Reactions

Liu

2019

Synthesis

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“…The unique structures of aspidospermidine and minfiensine have attracted considerable synthetic efforts. Although a number of beautiful total syntheses have been reported, the asymmetric syntheses of aspidospermidine 18 and minfiensine 19 using enantioselective catalytic methods remain scarce and highly desirable. Despite having different biological origins, both aspidospermidine and minfiensine share a common chiral hydrocarbazole skeleton bearing an all-carbon quaternary stereocenter.…”

Section: Resultsmentioning

confidence: 99%

Efficient syntheses of (−)-crinine and (−)-aspidospermidine, and the formal synthesis of (−)-minfiensine by enantioselective intramolecular dearomative cyclization

Yang

Guo

et al. 2017

Chem. Sci.

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“…Starting from the 2,3-disubstituted indole 178, the domino strategy based on the asymmetric indole dearomatization/iminium cyclization was applied in the synthesis of the tetracyclic core structure 179 that was used in the total synthesis of the indole alkaloid (+)-minfiensine (Scheme 72). 72 The best enantioselective result was obtained by us-ing 4.5 mol% of ligand (S,S)-L8 (89% ee). Furthermore, this method potentially gives access to other core structure of monoterpene indole alkaloids, such as vincorine, echitamine, and aspidosphylline A.…”

Section: Review Synthesismentioning

confidence: 99%

Pd-Catalyzed Domino Reactions Involving Alkenes To Access Substituted Indole Derivatives

et al. 2020

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Palladium-catalyzed domino reactions are advanced tools in achieving various nitrogen-containing heterocycles in an efficient and economical manner due to the reduced number of steps in the process. This review highlights recent advances in domino processes aimed at the synthesis of indole derivatives and polycyclic systems containing the indole nucleus in intra/intra- or intra/intermolecular reactions. In particular, we consider domino processes that involve a double bond in a step of the sequence, which allow the issue of regioselectivity in the cyclization to be faced and overcome. The different sections in this review focus on the synthesis of the indole nucleus and functionalization of the scaffold starting from different substrates that have been identified as activated starting materials, which involve a halogenated moiety or unactivated unsaturated systems. In the former case, the reaction is under Pd(0) catalysis, and in the second case a Pd(II) catalytic species is required and then an oxidant is necessary to reconvert the Pd(0) into the active Pd(II) species. On the other hand, the second method has the advantage that it uses easy available and inexpensive substrates.1 Introduction2 Indole Scaffold Synthesis2.1 Activated Substrates2.2 Unactivated Substrates3 Functionalization of Indole Scaffold3.1 Activated Substrates3.2 Unactivated Substrates4 Conclusions

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Total Synthesis of (+)‐Minfiensine: Construction of the Tetracyclic Core Structure by an Asymmetric Cascade Cyclization

Cited by 54 publications

References 61 publications

Base-Metal-Catalyzed Olefin Isomerization Reactions

Base-Metal-Catalyzed Olefin Isomerization Reactions

Efficient syntheses of (−)-crinine and (−)-aspidospermidine, and the formal synthesis of (−)-minfiensine by enantioselective intramolecular dearomative cyclization

Pd-Catalyzed Domino Reactions Involving Alkenes To Access Substituted Indole Derivatives

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