Synthesis of the B/C-ring system of tetronasin (ICI-139603).

Hori, Kazuyuki; Mori, Shuho; Nomura, Keiichi; Inagaki, Atsushi; Yoshii, Eiichi

doi:10.1248/cpb.38.1784

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Synthesis Of the C 5 −C 13 Fragment1

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Cited by 8 publications

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“…Lactonization with t -BuOK, followed by in-situ equilibration of the C 6 stereocenter, provided 508 in 86% yield. Ring opening of the lactone with Me 2 AlNH 2 followed by oxidation completed the synthesis of the C 5 −C 13 fragment in 15 steps and 12% overall yield 110 …”

Section: Synthesis Of the C 5 −C 13 Fragmentmentioning

confidence: 99%

Strategy and Methodology Development for the Total Synthesis of Polyether Ionophore Antibiotics

2000

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Section: Synthesis Of the C 5 −C 13 Fragmentmentioning

confidence: 99%

Strategy and Methodology Development for the Total Synthesis of Polyether Ionophore Antibiotics

2000

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“…Tetronasin has been evaluated as a growth accelerator for cattle and as an antiparasitic agent. 3,4 The first and only total syntheses of Tetronomycin 5 and Tetronasin [6][7][8] were reported by Yoshii and co-workers in 1992 and 1993, respectively. Markworthy features of these syntheses include: (a) a ZrCl 4 -catalysed insertion of an a-diazoester into the C-H of an aldehyde to generate a key b-keto ester intermediate required for the construction of the tetronic acid moiety, and (b) a reductive cyclisation that creates the cyclohexane ring with high diastereoselectivity.…”

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confidence: 99%