Total Synthesis of a Tetracyclic Anti-tumor, UCE6.

Tatsuta, Kuniaki; Inukai, Takayuki; Itoh, Sayaka; Kawarasaki, Masataka; Nakano, Yuko

doi:10.7164/antibiotics.55.1076

Cited by 12 publications

(5 citation statements)

References 8 publications

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“…In the pioneering work of Hauser and Mal, it is amply demonstrated that decalenones can be annulated to give naphthacenedione of 11-deoxyanthracyclines in which A rings are nonaromatic. Tatsuta et al showed that a similar strategy could be applicable to the synthesis of the naphthacenedione skeleton of UCE6 ( 173 ), an antitumor antibiotic that contains an aromatic A ring. They accomplished the total synthesis in a regiospecific manner in 24 steps.…”

Section: 2 Cycloalkenonesmentioning

confidence: 99%

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Recent Advances in the Hauser Annulation

2007

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Section: 2 Cycloalkenonesmentioning

confidence: 99%

“…Tatsuta et al 65 showed that the furanone ring of an isobenzofuranone, e.g., 168, can be directly built up from ortho-formylated benzamide 351 by reacting with sodium benzenesulfinate at 80 °C in acetic acid medium (Scheme 78). A similar principle was used for phenolic phthalide sulfone.…”

Section: Preparation Of Isobenzofuranonesmentioning

confidence: 99%

Recent Advances in the Hauser Annulation

2007

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“…By this methodology, we have already achieved total syntheses of bioactive natural products including nanaomycins, kalafungin, medermycin, MS‐444, PF1092s, ES‐242s, tetracycline, napyradiomycin A1, UCE‐6, BE‐54238B, BE‐52440A, lactonamycin, K1115 B 1α and K1115 B 1β (Figure ).…”

Section: The Key Methodologies and The Background Of Our Strategy 1: 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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“…Scheme 13 Scheme 14 The first total synthesis of the tetracyclic compound (±)-UCE6 (74) was also accomplished using a phthalide annulation strategy. 24 Lithium hexamethyldisilazide was used to deprotonate phthalide 71, thereby initiating annulation with cyclohexenone 72 to produce intermediate 73 upon oxidation with benzyl methyl ether in the presence of palladium-on-carbon (Scheme 21).…”

Section: Scheme 19mentioning

confidence: 99%