Total Syntheses of (−)‐Conidiogenone B, (−)‐Conidiogenone, and (−)‐Conidiogenol

Xu, Bo; Xun, Wen; Su, Shaobin; Zhai, Hongbin

doi:10.1002/ange.202007247

Cited by 6 publications

(1 citation statement)

References 57 publications

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“…31 In 2011, the Sensuki group reported a mechanistic study using Ni(0)-PCy3 to effect oxidative cyclization of alkenyl-aryl nitriles to form a metallacycle with triflic acid as additive to activate the nitrile moiety. 32 In two other examples, Fe(acac)3 and Mn(dmp)3-catalyzed alkenyl nitrile cyclizations involving five-membered ring formation 33 or in a rigid framework. 34 With these precedents in mind, we tested numerous HAT and transition metal-catalyzed conditions Scheme 8.…”

Section: Second Generation Approachmentioning

confidence: 99%

Evolution of a Strategy for the Unified, Asymmetric Total Syntheses of DMOA-Derived Spiromeroterpenoids

yang,

Oladokun,

Porco, Jr

2024

Preprint

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DMOA-derived spiromeroterpenoids are a group of natural products with complex structures and varied biological activities. Recently, we reported the first enantioselective total synthesis of five spiromeroterpenoids based on a fragment coupling strategy. This full account describes details of a strategy evolution that culminated in successful syntheses of the targeted natural products. Although our alkylative dearomatization methodology was unable to deliver the desired spirocyclic product in our first-generation approach, our second-generation approach based on oxidative [3+2] cycloaddition produced the asnovolin H core along with several complex dimers. Challenges with the dearomatization approach finally led us to develop a third generation, non-dearomatization approach based on a fragment coupling strategy to construct the conserved, sterically hindered bis-neopentyl linkage of the spiromeroterpenoids through 1,2-addition. To enable scalable access of the natural products, a refined, multigram-scale synthesis of the coupling partners was developed. A series of stereoselective transformations was developed through judicious choice of reagents and conditions. Finally, modular spirocycle construction logic was demonstrated through the synthesis of a small library of spiromer-oterpenoid analogues.

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Section: Second Generation Approachmentioning

confidence: 99%

Evolution of a Strategy for the Unified, Asymmetric Total Syntheses of DMOA-Derived Spiromeroterpenoids

yang,

Oladokun,

Porco, Jr

2024

Preprint

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Strategic Applications of the β‐Silicon Effect

Roberts

McLaughlin

2022

Adv Synth Catal

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Organosilicon reagents are highly versatile and privileged scaffolds in modern synthetic chemistry, largely due to the range of transformations the groups are amenable to. The β‐Silicon effect is one of the fundamental phenomena underpinning the inherent reactivity of organosilicon reagents, allowing unsaturated organosilanes to undergo a range of electrophilic substitutions with a variety of nucleophiles. The application of the β‐Silicon effect in a range of organic transformations is reviewed with the discussion divided up based on the class of silane. The reactivity of these compounds towards carbon, heteroatom and metallic electrophiles is discussed from classical applications such as the Sakurai allylation to contemporary applications such as cross‐coupling chemistry. In addition, examples of these transformations in the context of methodology development and natural product synthesis are provided.

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Synthetic Studies to Fused 5/5/6‐Tricyclic Frameworks: Access to Presilphiperfolanol Analogues and A, B, C‐Ring System of Lycopodium Alkaloids and Cyclopiane Diterpenes

Kotha

Keesari

2022

Eur J Org Chem

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Herein, we describe new synthetic approaches to fused 5/5/6‐carbocyclic frameworks present in various polycyclic natural products such as presilphiperfolanols, lycopodium alkaloids, and cyclopiane diterpenes. Our work features, a strategically introduced hydroxy group at the tert‐carbon center of the tricyclic system which is present in presilphiperfolanols. In addition, one presilphiperfolanol analogue is reported to show the potential of strategies disclosed in this work. All the new compounds are characterized by high‐resolution NMR spectral data. The structures of critical compounds were confirmed by various chemical transformations and further supported by single‐crystal X‐ray diffraction data. Overall, our approach is simple and rely on readily available starting materials and involves a tandem‐metathesis sequence. The synthetic studies disclosed here are applicable to the synthesis of natural products and to design medicinally important targets.

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Total Syntheses of (−)‐Conidiogenone B, (−)‐Conidiogenone, and (−)‐Conidiogenol

Cited by 6 publications

References 57 publications

Evolution of a Strategy for the Unified, Asymmetric Total Syntheses of DMOA-Derived Spiromeroterpenoids

Evolution of a Strategy for the Unified, Asymmetric Total Syntheses of DMOA-Derived Spiromeroterpenoids

Strategic Applications of the β‐Silicon Effect

Synthetic Studies to Fused 5/5/6‐Tricyclic Frameworks: Access to Presilphiperfolanol Analogues and A, B, C‐Ring System of Lycopodium Alkaloids and Cyclopiane Diterpenes

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