Total Synthesis of Lajollamycin?B |
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| Authors: | Dr Tatsuya Nishimaru Dr Kohei Eto Dr Keita Komine Prof?Dr Jun Ishihara Prof?Dr Susumi Hatakeyama |
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| Institution: | 1. Graduate School of Biomedical Sciences, Nagasaki University, Bunkyo-machi, Nagasaki 8, 52-8521 Japan;2. Medical Innovation Center, Nagasaki University, Bunkyo-machi, Nagasaki, 852-8521 Japan |
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| Abstract: | The first total synthesis of lajollamycin B, a structurally novel nitro-tetraene spiro-β-lactone/γ-lactone antibiotic, is described. The convergent synthesis involves the construction of the C8′–C11′ nitrodienylstannane and its coupling with the segment prepared from the C1′–C7′ ω-iodoheptadienoic acid and the right-hand heterocyclic fragment, which has been utilized for our previous syntheses of oxazolomycin A. The revision of the geometry of the terminal Δ10′, 11′-double bond from E to Z is also described for the structure of natural lajollamycin B. |
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| Keywords: | antibiotics isomers natural products structure elucidation total synthesis |
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