Total Synthesis of (−)-Principinol C

Ma, Tianhao; Cheng, Humin; Pitchakuntla, Mallesham; Ma, Weihao; Jia, Yanxing

doi:10.1021/jacs.2c08694

Cited by 29 publications

(16 citation statements)

References 38 publications

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“…Over the past 50 years, the synthesis of grayanane natural products has attracted the interest of many synthetic chemists, leading to the development of five total synthesis approaches, as well as two unfinished syntheses [43]. Table 1 summarizes the completed total syntheses in terms of steps, yields, advantages and drawbacks.…”

Section: Discussionmentioning

confidence: 99%

Total synthesis of grayanane natural products

Fay¹,

Blieck²,

Kouklovsky³

et al. 2022

Beilstein J. Org. Chem.

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Grayananes are a broad family of diterpenoids found in Ericaceae plants, comprising more than 160 natural products. Most of them exhibit interesting biological activities, often representative of Ericaceae use in traditional medicine. Over the last 50 years, various strategies were described for the total synthesis of these diterpenoids. In this review, we survey the literature for synthetic approaches to access grayanane natural products. We will focus mainly on completed total syntheses, but will also mention unfinished synthetic efforts. This work aims at providing a critical perspective on grayanane synthesis, highlighting the advantages and downsides of each strategy, as well as the challenges remaining to be tackled.

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Section: Discussionmentioning

confidence: 99%

Total synthesis of grayanane natural products

Fay¹,

Blieck²,

Kouklovsky³

et al. 2022

Beilstein J. Org. Chem.

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“…Consequently, if possible, cycloaddition reactions are often the privileged options in synthetic design of ring molecules, particularly for carbocycles where heteroatoms as potential “biting points” are absent. For example, many elegant total syntheses of natural products have used the venerable Diels–Alder [4 + 2] cycloaddition as the key step for rapidly building six-membered rings or Pauson–Khand [2 + 2 + 1] cycloaddition for five-membered rings . In the reported cycloadditions over more than hundred years, apparently at least one π bond was required in the reactant molecule (Scheme A).…”

Section: Introductionmentioning

confidence: 99%

Selective [2σ + 2σ] Cycloaddition Enabled by Boronyl Radical Catalysis: Synthesis of Highly Substituted Bicyclo[3.1.1]heptanes

et al. 2023

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In contrast to the traditional and widely-used cycloaddition reactions involving at least a π bond component, a [2σ + 2σ] radical cycloaddition between bicyclo[1.1.0]butanes (BCBs) and cyclopropyl ketones has been developed to provide a modular, concise, and atom-economical synthetic route to substituted bicyclo[3.1.1]heptane (BCH) derivatives that are 3D bioisosteres of benzenes and core skeleton of a number of terpene natural products. The reaction was catalyzed by a combination of simple tetraalkoxydiboron(4) compound B 2 pin 2 and 3-pentyl isonicotinate. The broad substrate scope has been demonstrated by synthesizing a series of new highly functionalized BCHs with up to six substituents on the core with up to 99% isolated yield. Computational mechanistic investigations supported a pyridine-assisted boronyl radical catalytic cycle.

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“…A prominent example among these transformations is the Pauson–Khand reaction, a formal [2 + 2 + 1] cycloaddition between an alkene, an alkyne (or allene), and carbon monoxide (Scheme A). − This reaction enables rapid access to highly functionalized cyclopentenone scaffolds, a prevalent motif encountered in natural products and synthetic intermediates. − Traditionally, the Pauson–Khand reaction uses stoichiometric amounts of cobalt carbonyl (Co 2 (CO) 8 ) both as a carbon monoxide source and as a mediator to form three new C–C bonds from an alkyne and an alkene to generate cyclopentenone products. , …”

Section: Introductionmentioning

confidence: 99%

Intermolecular Pauson–Khand-Type Reaction of Vinyl Iodides with Alkynes and a CO Surrogate

et al. 2023

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A strategy for the palladium-catalyzed intermolecular synthesis of polysubstituted cyclopentenones is reported. The three-component reaction utilizes vinyl iodides and internal alkynes to form the carbon framework of the cyclopentenone with Cr(CO)6 serving as an easy to handle, solid CO surrogate, and a hydrosilane as a hydride source. We demonstrate the scope of the reaction which includes a wide range of functional groups. The reaction is regioselective, with the use of linear or branched vinyl iodides resulting in the α- or β-substituted cyclopentenones, respectively. Further, we show that a two-step sequence from commercially available alkynes can be used to generate cyclopentenone products via formation of the vinyl iodide and subsequent Pauson–Khand-type reaction.

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Total Synthesis of (−)-Principinol C

Cited by 29 publications

References 38 publications

Total synthesis of grayanane natural products

Total synthesis of grayanane natural products

Selective [2σ + 2σ] Cycloaddition Enabled by Boronyl Radical Catalysis: Synthesis of Highly Substituted Bicyclo[3.1.1]heptanes

Intermolecular Pauson–Khand-Type Reaction of Vinyl Iodides with Alkynes and a CO Surrogate

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