(+)-Sorangicin A synthetic studies. Construction of the C(1-15) and C(16-29) subtargets.
[structure: see text] Effective stereocontrolled syntheses of subtargets (-)-2 and (-)-4, comprising respectively the C(16-29) and C(1-15) tetrahydropyran and dihydropyran moieties of the potent antibiotic (+)-sorangicin A (1), have been achieved. The cornerstone for the synthesis of (-)-2 involved an aldol tactic exploiting 1,4-induction, followed in turn by an acid-mediated cyclization/ketalization and hydrosilane reduction promoted by TMSOTf, while construction of (-)-4 entailed a stereoselective conjugate addition/alpha-oxygenation sequence.
Smith
Amos B
AB
Department of Chemistry, Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, 19104, USA. smithab@sas.upenn.edu
Fox
Richard J
RJ
Vanecko
John A
JA
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D009231:Myxococcales / Q000737:chemistry; D013237:Stereoisomerism
D000617:Aminoglycosides; C051799:sorangicin A