Alternative Strategies for the Construction of Macrocycles

Santandrea, Jeffrey; Bédard, Anne‐Catherine; Léséleuc, Mylène de; Raymond, Michaël; Collins, Shawn K.

doi:10.1002/9781119092599.ch13

“…Among the numerous macrocyclic natural product syntheses over the past decades, the crucial ring closing was most commonly achieved via late-stage ring-closing metathesis, 10 − 12 macrolactonization, 13 , 14 or macrolactamization strategies ( Scheme 1 a). 15 − 17 The broad array of methods provided for these transformations in the literature set them as textbook approaches. This does not, however, detract from the fact that different retrosynthetic disconnections are possible.…”

Section: Introductionmentioning

confidence: 99%

Unconventional Macrocyclizations in Natural Product Synthesis

Saridakis

¹

,

Kaiser

²

,

Maulide

³

2020

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Over the past several decades, macrocyclic compounds have emerged as increasingly significant therapeutic candidates in drug discovery. Their pharmacological activity hinges on their rotationally restricted three-dimensional orientation, resulting in a unique conformational preorganization and a high enthalpic gain as a consequence of high-affinity macrocycle–protein binding interactions. Synthetic access to macrocyclic drug candidates is therefore crucial. From a synthetic point of view, the efficiency of macrocyclization events commonly suffers from entropic penalties as well as undesired intermolecular couplings (oligomerization). Although over the past several decades ring-closing metathesis, macrolactonization, or macrolactamization have become strategies of choice, the toolbox of organic synthesis provides a great number of versatile transformations beyond the aforementioned. This Outlook focuses on a selection of examples employing what we term unconventional macrocyclizations toward the synthesis of natural products or analogues.

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Planar Chirality: A Mine for Catalysis and Structure Discovery

López

¹

,

Palomo

²

2022

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Planar chirality is one of the most fascinating expressions of chirality, which is exploited by nature to lock three‐dimensional chiral conformations and, more recently, by chemists to create new chiral reagents, catalysts, and functional organic materials. Nevertheless, the shortage of procedures able to induce and secure asymmetry during the generation of these unique chiral entities has dissuaded chemists from exploiting their structural properties. This Minireview intends to illustrate the limited but remarkable catalytic methods that have been reported for the production of planar chirality in strained molecules and serve as a source of inspiration for the development of new unconventional procedures, which are expected to appear in the near future.

show abstract

Planar Chirality: A Mine for Catalysis and Structure Discovery

López

¹

,

Palomo

²

2022

View full text Add to dashboard Cite

Planar chirality is one of the most fascinating expressions of chirality, which is exploited by nature to lock three‐dimensional chiral conformations and, more recently, by chemists to create new chiral reagents, catalysts, and functional organic materials. Nevertheless, the shortage of procedures able to induce and secure asymmetry during the generation of these unique chiral entities has dissuaded chemists from exploiting their structural properties. This Minireview intends to illustrate the limited but remarkable catalytic methods that have been reported for the production of planar chirality in strained molecules and serve as a source of inspiration for the development of new unconventional procedures, which are expected to appear in the near future.

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Alternative Strategies for the Construction of Macrocycles

Cited by 3 publications

References 129 publications

Unconventional Macrocyclizations in Natural Product Synthesis

Unconventional Macrocyclizations in Natural Product Synthesis

Planar Chirality: A Mine for Catalysis and Structure Discovery

Planar Chirality: A Mine for Catalysis and Structure Discovery

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