859845-11-7Relevant articles and documents
(+)-Sorangicin A synthetic studies. Construction of the C(1-15) and C(16-29) subtargets
Smith III, Amos B.,Fox, Richard J.,Vanecko, John A.
, p. 3099 - 3102 (2005)
(Chemical Equation Presented) 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/α-oxygenation sequence.