Stereoselective synthesis of premisakinolide A, the monomeric counterpart of the marine 40-membered dimeric macrolide misakinolide A.
[structure: see text] The first synthesis of premisakinolide A, the monomeric counterpart of misakinolide A, the marine 40-membered macrolide displaying potent activity against a variety of human carcinoma cell lines, has been reported. The strategy was highlighted by a crucial coupling of a tetrahydropyran fragment and an alkynylaluminum reagent having a polypropionate chain, the highly stereoselective cross aldol reaction of segment A and segment B, and the stereospecific construction of the polypropionate structure based on original acyclic stereocontrol.
Nakamura
Ryoichi
R
Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo, Japan.
Tanino
Keiji
K
Miyashita
Masaaki
M
D000818:Animals; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D018942:Macrolides / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
D018942:Macrolides; C509581:premisakinolide A; C104924:bistheonellide A