TY - JOUR
T1 - Diastereoselective synthesis of 2,3,6-trisubstituted tetrahydropyran-4-ones via prins cyclizations of enecarbamates
T2 - A formal synthesis of (+)-ratjadone A
AU - Cossey, Kimberly N.
AU - Funk, Raymond L.
N1 - Copyright:
Copyright 2010 Elsevier B.V., All rights reserved.
PY - 2004/10/6
Y1 - 2004/10/6
N2 - Enecarbamates are shown to be excellent terminating groups for Prins cyclizations. A noteworthy feature of this methodology is the easy, stereoselective construction of the cyclization precursors by alkylation of metalated (E)-enecarbamates with epoxides. The stereochemistry of the resultant trisubstituted (E)-enecarbamates is then transferred with high fidelity to afford the frequently observed and biologically significant all-cis-2,3,6-trisubstituted tetrahydropyran substructures of naturally occurring compounds. Other substituted tetrahydropyrans, including 2,3,5,6-tetrasubstituted, cis-2,3-disubstituted, and cis-2,6-disubstituted, are also accessible. This methodology facilitated an exceptionally concise formal total synthesis of the nuclear export inhibitor (+)-ratjadone A.
AB - Enecarbamates are shown to be excellent terminating groups for Prins cyclizations. A noteworthy feature of this methodology is the easy, stereoselective construction of the cyclization precursors by alkylation of metalated (E)-enecarbamates with epoxides. The stereochemistry of the resultant trisubstituted (E)-enecarbamates is then transferred with high fidelity to afford the frequently observed and biologically significant all-cis-2,3,6-trisubstituted tetrahydropyran substructures of naturally occurring compounds. Other substituted tetrahydropyrans, including 2,3,5,6-tetrasubstituted, cis-2,3-disubstituted, and cis-2,6-disubstituted, are also accessible. This methodology facilitated an exceptionally concise formal total synthesis of the nuclear export inhibitor (+)-ratjadone A.
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U2 - 10.1021/ja046940r
DO - 10.1021/ja046940r
M3 - Article
C2 - 15453725
AN - SCOPUS:4644259961
SN - 0002-7863
VL - 126
SP - 12216
EP - 12217
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 39
ER -