Stereocontrolled total synthesis and biological evaluation of (−)- and (+)-petrosin and its derivatives

Toya, Hiroki; Satoh, Takahito; Okano, Kentaro; Takasu, Kiyosei; Ihara, Masataka; Takahashi, Atsushi; Tanaka, Haruo; Tokuyama, Hidetoshi

doi:10.1016/j.tet.2014.08.009

Cited by 14 publications

(6 citation statements)

References 37 publications

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“…Subsequently, 2-pyridylacetyl-CoA (74) and malonyl-CoA (76) underwent condensation, generating a diketide intermediate by a type III PKS. This intermediate (77) suffered from intramolecular cyclization, producing quinolizinone scaffolds (78)(79)(80)(81)(82). This work may provide an entirely new approach to the enzymatic synthesis of pharmaceutically important alkaloids.…”

Section: Enzymatic and Chemoenzymatic Approaches For Alkaloidsmentioning

confidence: 99%

“…For this reason, the development of a synthetic strategy to provide a large amount of petrosins and the creation of new analogues with modified/improved biological activity have been important research topics in the field of organic chemistry. Toya et al accomplished total synthesis of (−)-and (+)-petrosins with lipase-mediated desymmetrization of 1,3-diol as the key step (Scheme 7) [79]. The chemoenzymatic preparation of the bisquinolizidine alkaloid, (−)-and (+)-petrosin, was achieved by using several steps.…”

Section: Enzymatic and Chemoenzymatic Approaches For Alkaloidsmentioning

confidence: 99%

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Recent Advances in the Synthesis of Marine-Derived Alkaloids via Enzymatic Reactions

et al. 2022

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Alkaloids are a large and structurally diverse group of marine-derived natural products. Most marine-derived alkaloids are biologically active and show promising applications in modern (agro)chemical, pharmaceutical, and fine chemical industries. Different approaches have been established to access these marine-derived alkaloids. Among these employed methods, biotechnological approaches, namely, (chemo)enzymatic synthesis, have significant potential for playing a central role in alkaloid production on an industrial scale. In this review, we discuss research progress on marine-derived alkaloid synthesis via enzymatic reactions and note the advantages and disadvantages of their applications for industrial production, as well as green chemistry for marine natural product research.

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Section: Enzymatic and Chemoenzymatic Approaches For Alkaloidsmentioning

confidence: 99%

Section: Enzymatic and Chemoenzymatic Approaches For Alkaloidsmentioning

confidence: 99%

Recent Advances in the Synthesis of Marine-Derived Alkaloids via Enzymatic Reactions

et al. 2022

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“… 63 In their chemo-enzymatic synthesis of the marine sponge alkaloid (−)-petrosin (79, Scheme 11 ), Hidetoshi Tokuyama and co-workers managed to prevent this side reaction by immediate silyl-protection of the free hydroxyl group. 64 Hence, they reacted diol 73 with vinyl acetate under lipase PS 37 catalysis, and – after filtration and evaporation of excess acyl donor – treated the crude monoacetate with TBDMS chloride to give compound ( S )-74 in 84% yield (two steps) and 99% ee . This building block was elaborated into the piperidine derivative 75, which in turn served as precursor to vinylic iodide 76 and borane 77.…”

Section: Biocatalytic Asymmetric Synthesis Of Chiral Building Blocksmentioning

confidence: 99%

The role of biocatalysis in the asymmetric synthesis of alkaloids – an update

et al. 2021

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“… , In comparison with TIPSOTf and Sc(OTf) 3 , triflimide exhibited better catalytic activity, leading to a faster reaction rate. A similar process modified from this protocol was later applied in the synthesis of the natural product petrosin and its derivatives …”

Section: Reactions Catalyzed or Mediated By Triflimidementioning

confidence: 99%

Triflimide (HNTf₂) in Organic Synthesis

2018

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Triflimide (HNTf2) is a commercially available and highly versatile super Brønsted acid. Owing to its strong acidity as well as good compatibility with organic solvents, it has been widely employed as an exceptional catalyst, promoter, or additive in a wide range of organic reactions. On many occasions, triflimide has been demonstrated to outperform triflic acid (TfOH). The uniquely outstanding performance of triflimide also benefits from the low nucleophilicity and noncoordinating property of its conjugate base (Tf2N–). Therefore, it has been employed as a precursor toward a variety of cationic metal complexes or organic intermediates with enhanced reactivity or catalytic activity. In this Review, we describe these features and applications of triflimide in organic synthesis, including its synthesis, physical properties, and role as catalyst or promoter in organic reactions. At the end of this Review, another closely related reagent, triflidic acid (HCTf3), is also briefly introduced.

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Stereocontrolled total synthesis and biological evaluation of (−)- and (+)-petrosin and its derivatives

Cited by 14 publications

References 37 publications

Recent Advances in the Synthesis of Marine-Derived Alkaloids via Enzymatic Reactions

Recent Advances in the Synthesis of Marine-Derived Alkaloids via Enzymatic Reactions

The role of biocatalysis in the asymmetric synthesis of alkaloids – an update

Triflimide (HNTf₂) in Organic Synthesis

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Stereocontrolled total synthesis and biological evaluation of (−)- and (+)-petrosin and its derivatives

Cited by 14 publications

References 37 publications

Recent Advances in the Synthesis of Marine-Derived Alkaloids via Enzymatic Reactions

Recent Advances in the Synthesis of Marine-Derived Alkaloids via Enzymatic Reactions

The role of biocatalysis in the asymmetric synthesis of alkaloids – an update

Triflimide (HNTf2) in Organic Synthesis

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Product

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Triflimide (HNTf₂) in Organic Synthesis