Natural product total synthesis using rearrangement reactions

Chao, Lu; Li, Guang; Zu, Liansuo

doi:10.1039/d2qo01040b

Cited by 18 publications

(13 citation statements)

References 63 publications

(41 reference statements)

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“…Specifically, our cyclopentanone-based approach could allow the coupling of diazo-cyclopentanone 10 (made from (−)-methyl jasmonate) and 2-aminobenzaldehyde 11 through the N–H insertion/intramolecular aldol reaction ( II )/carbonyl 1,2-migration to afford the key intermediate 12 (Scheme ). , The ester, alkene, and carbonyl groups in 12 then could serve as the synthetic handles to construct the remaining bridged ring system shown in (+)-gilbertine.…”

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confidence: 65%

Total Synthesis of (+)-Gilbertine: A Cyclopentanone-Based Approach

Wei

Peng

2022

Org. Lett.

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confidence: 65%

Total Synthesis of (+)-Gilbertine: A Cyclopentanone-Based Approach

Wei

Peng

2022

Org. Lett.

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“…Skeletal rearrangement of carbocations or carbonium ions has been serving as one of the potential routes to arrive at various synthetically challenging targets, which by other means would be difficult to achieve. [1][2][3][4] Further their propelling efficiency towards alternation has placed themselves at an exceptionally eventful residence and perhaps due to this particular reason, these electrically charged species have been used widely in synthetic organic chemistry. Among the various rearrangements listed in literature operating on the existence of a carbocation intermediate, pinacol rearrangement and semipinacol rearrangement are arguably the most encountered ones.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Radical‐Polar Crossover Non‐Classical Semipinacol Rearrangements: The Sustainable Approach

Nanda

2023

Adv Synth Catal

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Semipinacol rearrangement has brought several elegant methods for the rapid synthesis of various complex scaffolds and as a result, has been applied extensively in the total synthesis of natural products. Apart from the classical ways, where transition metal or acids catalyzes the formation of carbocation, the semipinacol rearrangement has seen numerous revolutions and now are being happening in an eco-friendly manner relying on a catalytic radical-polar crossover tool. These catalytic processes are mainly occurring through photocatalysis or electrocatalysis. This review will provide a brief idea of these developments. 1. Introduction 2. Photocatalytic Radical-Polar Crossover 3. Electrocatalytic Radical-Polar Crossover 4. Metal-Free Radical-Polar Crossover 5. Conclusion and Outlook

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“…In this context, rearrangement reactions [ 22 , 23 , 24 , 25 ] offer a versatile way to generate the target structures through the bond reorganization of the intermediate precursors. Rearrangement reactions allow the straightforward formation of the core skeletons, the control of stereochemistry, and the identification of potential commercially available synthons.…”

Section: Introductionmentioning

confidence: 99%

Unifying the Synthesis of a Whole Family of Marine Meroterpenoids through a Biosynthetically Inspired Sequence of 1,2-Hydride and Methyl Shifts as Key Step

2023

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Marine meroterpenoids have attracted a great deal of attention from synthetic research groups due to their attractive and varied biological activities and their unique and diverse structures. In most cases, however, further biological studies have been severely limited mainly to the scarcity of natural supply and because almost none of the reported syntheses methods has enabled unified access for a large number of marine meroterpenoids with aureane and avarane skeletons. Based on our previous publications and the study of recent manuscripts on marine meroterpenoids, we have conceived a unified strategy for these fascinating marine compounds with aureane or avarane skeletons using available drimane compounds as starting materials. The key step is a biosynthetic sequence of 1,2-hydride and methyl shifts. This strategy is of great synthetic value to access marine meroterpenoids through easy chemical synthetic procedures. Finally, several retrosynthetic proposals are made for the future synthesis of several members of this class of meroterpenoids, focused on consolidating these 1,2-rearrangements as a versatile and unified strategy that could be widely used in the preparation of these marine meroterpenoids.

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Natural product total synthesis using rearrangement reactions

Abstract: Total synthesis of natural products has been an important pursuit in chemical synthesis due to the fascinating structural complexity and/or interesting biological activities. In most synthetic designs, the rapid construction...

Cited by 18 publications

References 63 publications

Total Synthesis of (+)-Gilbertine: A Cyclopentanone-Based Approach

Total Synthesis of (+)-Gilbertine: A Cyclopentanone-Based Approach

Catalytic Radical‐Polar Crossover Non‐Classical Semipinacol Rearrangements: The Sustainable Approach

Unifying the Synthesis of a Whole Family of Marine Meroterpenoids through a Biosynthetically Inspired Sequence of 1,2-Hydride and Methyl Shifts as Key Step

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