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The Total Synthesis of Inostamycin A

Title
The Total Synthesis of Inostamycin A
Authors
Yu, GuangriJung, ByunghyuckLee, Hee-SeungKang, Sung Ho
DGIST Authors
Jung, Byunghyuck
Issue Date
2016-02-12
Citation
Angewandte Chemie: International Edition, 55(7), 2573-2576
Type
Article
Article Type
Article
Keywords
AcetoneAddition ReactionsAldehydesAldol ReactionsAsymmetric Aldol ReactionsCarbonChemical ReactionsChiral Building BlocksCondensationCondensation ReactionsDiastereoselective AdditionsEfficiencyInostamycin AKetonesQuaternary StereocentersRetrosynthesisStereogenic CentersStereoselectivitySynthesis (Chemical)Total Synthesis
ISSN
1433-7851
Abstract
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. The total synthesis of inostamycin A sodium salt was completed through a stereoselective and efficient aldol condensation of aldehyde A with the lithium enolate of ethyl ketone B. The two quaternary carbons at C20 and C16 of B were installed by diastereoselective addition reactions of the transmetalated species from iodides to ketones. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
URI
http://hdl.handle.net/20.500.11750/5119
DOI
10.1002/anie.201510852
Publisher
Wiley-VCH Verlag
Related Researcher
Files:
There are no files associated with this item.
Collection:
School of Undergraduate Studies1. Journal Articles


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