TY - JOUR
T1 - Synthetic studies on nemorosone via enantioselective intramolecular cyclopropanation
AU - Abe, Masahito
AU - Saito, Aya
AU - Nakada, Masahisa
N1 - Funding Information:
This work was supported in part by a Waseda University Grant for Special Research Projects, a Grant-in-Aid from JSPS and MEXT, and the Global COE program ‘Center for Practical Chemical Wisdom’ by MEXT. The fellowship for young scientists to M.A. from JSPS is also gratefully acknowledged.
Copyright:
Copyright 2010 Elsevier B.V., All rights reserved.
PY - 2010/3/3
Y1 - 2010/3/3
N2 - This Letter describes synthetic studies of nemorosone via enantioselective intramolecular cyclopropanation. For the total synthesis of nemorosone, three potential intermediates were evaluated through the efficiency of three sequential reactions, namely, their intramolecular cyclopropanation, dimethylation of the resultant cyclopropanes, and ring-opening reaction of the alkylated cyclopropanes. As a result, α-diazomethyl ketone 10c was found to be the most suitable. The enantioselective intramolecular cyclopropanation to construct the bicyclo[3.3.1]nonane core and preparation of the compound with all the correct stereogenic centers of nemorosone are also described.
AB - This Letter describes synthetic studies of nemorosone via enantioselective intramolecular cyclopropanation. For the total synthesis of nemorosone, three potential intermediates were evaluated through the efficiency of three sequential reactions, namely, their intramolecular cyclopropanation, dimethylation of the resultant cyclopropanes, and ring-opening reaction of the alkylated cyclopropanes. As a result, α-diazomethyl ketone 10c was found to be the most suitable. The enantioselective intramolecular cyclopropanation to construct the bicyclo[3.3.1]nonane core and preparation of the compound with all the correct stereogenic centers of nemorosone are also described.
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U2 - 10.1016/j.tetlet.2009.12.147
DO - 10.1016/j.tetlet.2009.12.147
M3 - Article
AN - SCOPUS:74749108885
VL - 51
SP - 1298
EP - 1302
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 9
ER -