TY - JOUR
T1 - Synthesis of γ-lactones by desymmetrization. A synthesis of (-)-muricatacin
AU - Teresa Barros, M.
AU - Adilia Januario Charmier, M.
AU - Maycock, Christopher D.
AU - Michaud, Thierry
PY - 2009/1/3
Y1 - 2009/1/3
N2 - A short synthesis of the natural potent cytotoxic agent (-)-muricatacin 1 and related unsaturated lactones from a versatile common intermediate, dienedioate 2, derived from d-mannitol or tartaric acid, is described. The strategy depends upon the desymmetrization of 7 by dihydroxylation and elaboration of the hydroxy alkyl sidechain. A route to unsaturated lactones is also described using a cis selective Wittig reaction. Since the enantiomers of 2 are available from the corresponding tartaric acids, this method provides access to both enantiomers of the described compounds and a wide range of derivatives.
AB - A short synthesis of the natural potent cytotoxic agent (-)-muricatacin 1 and related unsaturated lactones from a versatile common intermediate, dienedioate 2, derived from d-mannitol or tartaric acid, is described. The strategy depends upon the desymmetrization of 7 by dihydroxylation and elaboration of the hydroxy alkyl sidechain. A route to unsaturated lactones is also described using a cis selective Wittig reaction. Since the enantiomers of 2 are available from the corresponding tartaric acids, this method provides access to both enantiomers of the described compounds and a wide range of derivatives.
KW - Desymmetrization
KW - Enantioselective
KW - Enoate
KW - γ-Lactones
UR - http://www.scopus.com/inward/record.url?scp=57049095842&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2008.10.020
DO - 10.1016/j.tet.2008.10.020
M3 - Article
AN - SCOPUS:57049095842
SN - 0040-4020
VL - 65
SP - 396
EP - 399
JO - Tetrahedron
JF - Tetrahedron
IS - 1
ER -