4.5 Article

Synthesis of (-)-tabtoxinine-β-lactam, the phytotoxin of tobacco wildfire disease

Journal

SYNTHESIS-STUTTGART
Volume -, Issue 16, Pages 2471-2480

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-2007-983785

Keywords

tabtoxinine-beta-lactam; beta-lactam; amino acids; total synthesis; natural products

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Synthesis of (-)-tabtoxinine-p-lactam and its (3R)-isomer, the cause of tobacco wildfire disease, was achieved from Lserine using a zinc-mediated coupling reaction, Sharpless asymmetric dihydroxylation and lactainization of beta-mesyloxy benzylhydroxamate amide as the key steps.

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