RCM/PCC oxidation strategy for synthesis of functionalized cyclic α,β-unsaturated lactones: synthesis of (+)-triacetoxygoniotriol and its diastereomers

• Published in: Tetrahedron Vol. 62; no. 48; pp. 11165 - 11171
• Main Authors: Srikanth, G.S.C., Krishna, Urlam Murali, Trivedi, Girish K., Cannon, John F.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 27.11.2006; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Goniotriol; Physical Sciences; RCM and PCC oxidation; Science & Technology; Styryllactones; Goniotriol; RCM and PCC oxidation; Styryllactones; (+)-GONIOPYPYRONE; styryllactones; GONIOTHALAMUS-GIGANTEUS ANNONACEAE; (+)-GONIOTRIOL; 8-ACETYLGONIOTRIOL; (+)-GONIOFUFURONE; GONIOFUFURONE; PYRIDINIUM CHLOROCHROMATE; STYRYL-LACTONES; (+)-ALTHOLACTONE; goniotriol; RING

A novel methodology leading to the synthesis of (+)-triacetoxygoniotriol 2 from d-glucose is described. Construction of the core six-membered α,β-unsaturated lactone moiety involved ring closing metathesis (RCM) followed by a PCC oxidation. Later exploiting the pseudo-symmetry of d-glucose three oth...