Total Synthesis of Selected Bioactive Natural Products:  Illustration of Strategy and Design

Tatsuta, Kuniaki; Hosokawa, Seijiro

doi:10.1021/cr040630+

Cited by 77 publications

(12 citation statements)

References 175 publications

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“…One of these approaches, the Sonogashira‐type coupling cyclization reaction works for a very wide range of substrates, but requires the use of superstoichiometric amounts of bases . The latter feature[25b] limits the substrate scope, especially in total synthesis, because it requires additional protecting/de‐protecting steps …”

Section: Introductionmentioning

confidence: 99%

“…[27] The latter feature [25b] limits the substrate scope, especially in total synthesis, because it requires additional protecting/de-protecting steps. [28] By reacting 1-Phenyl-1,2-benziodoxol-3-(1H)-one (1) with phenylacetylene (5a) with only Cu I as catalyst, we have serendipitously discovered the direct, regioselective synthesis of phthalides 6, in a Pd-free Sonogashira-like coupling reaction. The reaction proceeds under mild conditions and does not require the addition of a base.…”

Section: Introductionmentioning

confidence: 99%

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1‐Phenyl‐1,2‐benziodoxol‐3‐(1H)‐one as Synthon for Phthalide Synthesis through Pd‐Free, Base‐Free, Sonogashira‐Type Coupling Cyclization Reaction

Almasalma

Mejía

2017

Eur J Org Chem

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Hypervalent iodine(III) five‐membered heterocycles have found broad application as atom‐transfer reagents for organic synthesis. Among them, 1‐phenyl‐1,2‐benziodoxol‐3‐(1H)‐one is known as a traditional benzyne precursor, but no further synthetic applications have been reported. Herein, we report the first synthetic application of 1‐phenyl‐1,2‐benziodoxol‐3‐(1H)‐one to the synthesis of phthalides by using only CuI as catalyst. High selectivity and yields were achieved under mild reaction conditions with good functional group tolerance. During our investigations, the efficiency of different CuI and CuII catalysts under various reaction conditions were studied. The nature of the leaving group, the substituents on the substrate, and the temperature play an important role on both yield and selectivity. Moreover, a plausible mechanistic pathway for this transformation was proposed based on our observations and previous literature reports.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

1‐Phenyl‐1,2‐benziodoxol‐3‐(1H)‐one as Synthon for Phthalide Synthesis through Pd‐Free, Base‐Free, Sonogashira‐Type Coupling Cyclization Reaction

Almasalma

Mejía

2017

Eur J Org Chem

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“…In Tatsuta's laboratory the multifunctionalized cyclohexanes have been synthesized from carbohydrates . In the first total synthesis of tetracycline, the multifunctionalized cyclohexanone moiety was constructed from glucosamine (Scheme ).…”

Section: The Key Methodologies and The Background Of Our Strategy 2: mentioning

confidence: 99%

Total Synthesis of Hibarimicinone, a v‐Src Tyrosine Kinase Inhibitor Possessing the Pseudo‐Dimer Structure of Tetracycline

Tatsuta

Hosokawa

2013

The Chemical Record

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The total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor possessing thirteen stereogenic centers and an axial chirality, has been achieved. The key step to constructing the eight-ring skeleton was the double Michael–Dieckmann-type cyclization (Hauser annulation) using a thiolactone pseudo-dimer. These synthetic studies indicated the efficiency of the thiolactone-employed route to synthesize the multiply functionalized polycyclic compounds. The ABCD-ring moiety including the bridging ether was constructed by a strategy including oxidation of the C-ring hydroquinone and the subsequent transfer of the oxidation stage to the neighboring ring. The atropisomer of hibarimicinone was also synthesized to confirm the structure of the natural product.

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“…These unique structures have drawn attention both for syntheses with developing new methodologies and for creation of novel biologically active compounds. During total syntheses of natural products possessing aromatic rings and oxygenated cyclohexanes, we developed a novel methodology to synthesize those structures in short steps with convergency, meaning tandem Michael-Dieckmann cyclization [1][2][3]. Herein, we describe the total syntheses of 1$4 using Micheal-Dieckmann cyclization combined with carbohydrate chemistry [1][2][3][4].…”

Section: The Total Syntheses Of Pyranonaphthoquinone Antibiotics Usinmentioning

confidence: 99%

Total syntheses of bioactive natural products from carbohydrates

Tatsuta

Hosokawa

2006

Science and Technology of Advanced Materials

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Total syntheses of bioactive natural products recently accomplished in our laboratories are described. They are classified by structures of target molecules and are focused on our original approach to their own structures. The target molecules include nanaomycin, kalafungin, BE-54238B, tetracycline, rosmarinecine, thienamycin, luminacines C 1 and C 2 , tetrodecamycin, cochleamycin A, and tubelactomicin A, which have been synthesized as optically pure form from carbohydrates.

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Total Synthesis of Selected Bioactive Natural Products: Illustration of Strategy and Design

Cited by 77 publications

References 175 publications

1‐Phenyl‐1,2‐benziodoxol‐3‐(1H)‐one as Synthon for Phthalide Synthesis through Pd‐Free, Base‐Free, Sonogashira‐Type Coupling Cyclization Reaction

1‐Phenyl‐1,2‐benziodoxol‐3‐(1H)‐one as Synthon for Phthalide Synthesis through Pd‐Free, Base‐Free, Sonogashira‐Type Coupling Cyclization Reaction

Total Synthesis of Hibarimicinone, a v‐Src Tyrosine Kinase Inhibitor Possessing the Pseudo‐Dimer Structure of Tetracycline

Total syntheses of bioactive natural products from carbohydrates

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