A modular approach to marine macrolide construction. 4. Assembly of C36-C51 and C29-C44 building blocks and evaluation of key coupling reactions targeting spongistatin 1 (altohyrtin A).
Routes have been developed for the stereocontrolled elaboration of two highly functionalized sectors of spongistatin 1. The approach to ring F takes advantage of B-alkyl Suzuki-Miyaura coupling to install the C44-C45 bond. The E-ring pyran moiety was generated by acylation of an alpha-sulfonyl carbanion, the stereogenic centers of which were incorporated by sequential asymmetric aldol reactions. [structure: see text].
Ciblat
Stephane
S
Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA.
Kim
Jungchul
J
Stewart
Catherine A
CA
Wang
Jizhou
J
Forgione
Pat
P
Clyne
Dean
D
Paquette
Leo A
LA
D000215:Acylation; D007202:Indicators and Reagents; D018942:Macrolides / Q000138:chemical synthesis*; D008387:Marine Toxins / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis; D000095702:Polyether Toxins
D007202:Indicators and Reagents; D018942:Macrolides; D008387:Marine Toxins; D014753:Vinyl Compounds; C083856:spongistatin 1; D000095702:Polyether Toxins