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Total Synthesis of Lajollamycin B
Author(s) -
Nishimaru Tatsuya,
Eto Kohei,
Komine Keita,
Ishihara Jun,
Hatakeyama Susumi
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901069
Subject(s) - zoology , biology
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 Δ 10′, 11′ ‐double bond from E to Z is also described for the structure of natural lajollamycin B.