Total synthesis of laidlomycin

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The synthesis of laidlomycin is described. With an established stereocontrolled synthetic route to the aldehyde 5, the known beta-keto phosphonate 4 was coupled with 5 and the resulting enone was subjected to a sequential hydrogenolysis/hydrogenation and equilibration process to effect the correct spiroketalization for the natural product. The stereogenic carbons were elaborated by desymmetrization for C12, allylation for C13, vanadyl-induced epoxidation for C16, Zn(BH4)(2) reduction for C17, a chiral building block for C18 and C24, Shi epoxidation for C20 and C21, Myers' alkylation for C22, and thermodynamic control for C25.
Publisher
ROYAL SOC CHEMISTRY
Issue Date
2016-02
Language
English
Article Type
Article
Keywords

STEREOCONTROLLED TOTAL-SYNTHESIS; POLYETHER ANTIBIOTICS; ASYMMETRIC EPOXIDATION; OXIDATIVE CYCLIZATION; ZINC BOROHYDRIDE; CARBOXYLIC-ACIDS; NATURAL-PRODUCTS; METHYL-ESTERS; ALCOHOLS; MONENSIN

Citation

CHEMICAL COMMUNICATIONS, v.52, no.17, pp.3536 - 3539

ISSN
1359-7345
DOI
10.1039/C5CC10673G
URI
http://hdl.handle.net/10203/207656
Appears in Collection
CH-Journal Papers(저널논문)
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