The Total Synthesis of Inostamycin A

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The first total synthesis of inostamycin A is described. With efficient and stereoselective synthetic routes to aldehyde 3 and ketone 4 developed through asymmetric aldol reactions, addition reactions and reduction, and with chiral building blocks, the two large fragments were coupled with remarkable anti stereoselectivity and efficiency by aldol condensation. The coupling reaction provided the complete carbon skeleton with all the requisite functional groups and stereogenic centers for inostamycin A. The two quaternary carbons at C20 and C16 of ketone 4 were elaborated in a highly stereocontrolled manner by addition reactions of the transmetallated 5 to ethyl ketone 6 and the transmetallated 7 to methyl ketone 8, respectively, in which the use of LaCl3 for transmetallation was critical for high coupling efficiency.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2016-02
Language
English
Article Type
Article
Keywords

INOSITOL TRANSFERASE; CARBONYL-COMPOUNDS; NATURAL-PRODUCTS; CDP-DG; OXIDATION; ALCOHOLS; INHIBITOR; KETONES; ANTIBIOTICS; REDUCTION

Citation

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.55, no.7, pp.2573 - 2576

ISSN
1433-7851
DOI
10.1002/anie.201510852
URI
http://hdl.handle.net/10203/207428
Appears in Collection
CH-Journal Papers(저널논문)
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