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

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...

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Bibliographic Details
Published inTetrahedron 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
LanguageEnglish
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
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Summary: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 other diastereomers of triacetoxygoniotriol were synthesized using the developed methodology. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.09.016