We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
The Total Synthesis of Inostamycin A.
- Authors
Yu, Guangri; Jung, Byunghyuck; Lee, Hee‐Seung; Kang, Sung Ho
- 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.
- Subjects
ORGANIC synthesis; NATURAL products; ALDOL condensation; COUPLING reactions (Chemistry); STEREOSELECTIVE reactions
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 7, p2619
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201510852