Total Synthesis of Lajollamycin B

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 a...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-06, Vol.25 (33), p.7927-7934
Main Authors: Nishimaru, Tatsuya, Eto, Kohei, Komine, Keita, Ishihara, Jun, Hatakeyama, Susumi
Format: Article
Language:English
Subjects:
Antibiotics
Chemistry
isomers
natural products
structure elucidation
Synthesis
total synthesis
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Summary: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. A synthesis of two halves: The first total synthesis of lajollamycin B in naturally occurring form is described. The synthesis involves Stille coupling of the C8′–C11′ nitrodienylstannane with the segment prepared by amidation of the C1′–C7′ ω‐iodoheptadienoic acid and the right‐hand heterocyclic fragment (see scheme). A revision of the geometry of the terminal Δ10′, 11′‐double bond from E to Z is also described.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201901069