TY - JOUR
T1 - Synthesis of Tricyclic Spiranoid Lactones via I2/Sm(II)- and I2/Pd(0)-Mediated Cyclizations of a Common Cycloalkylmethylene Precursor
AU - Mostinski, Yelena
AU - Valerio, Viviana
AU - Lankri, David
AU - Tsvelikhovsky, Dmitry
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/11/6
Y1 - 2015/11/6
N2 - A general synthesis of phylogenetically and structurally different tricyclic angularly fused spiranoid lactones, frequently observed as scaffold segments of various biochemical compounds and drugs of natural origin, is demonstrated via controlled cyclization of simple and easily accessible cycloalkylmethylene key precursors. The rapid composition of the key architecture yields an assembly of stable bicyclic iodolactones, which are converted to form a wide range of angularly fused tricyclic scaffolds.
AB - A general synthesis of phylogenetically and structurally different tricyclic angularly fused spiranoid lactones, frequently observed as scaffold segments of various biochemical compounds and drugs of natural origin, is demonstrated via controlled cyclization of simple and easily accessible cycloalkylmethylene key precursors. The rapid composition of the key architecture yields an assembly of stable bicyclic iodolactones, which are converted to form a wide range of angularly fused tricyclic scaffolds.
UR - http://www.scopus.com/inward/record.url?scp=84946780080&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.5b01278
DO - 10.1021/acs.joc.5b01278
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AN - SCOPUS:84946780080
SN - 0022-3263
VL - 80
SP - 10464
EP - 10473
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 21
ER -