TY - JOUR
T1 - Synthetic studies on phloroglucins
T2 - a new approach to the bicyclo[3.3.1]nonane system via the regioselective ring-opening of the methoxycyclopropane
AU - Abe, Masahito
AU - Nakada, Masahisa
N1 - Funding Information:
This work was financially supported in part by a Waseda University Grant for Special Research Projects and a Grant-in-Aid for Scientific Research on Priority Areas (Creation of Biologically Functional Molecules (No. 17035082)) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan. We are also indebted to 21COE ‘Practical Nano-Chemistry’.
PY - 2007/7/9
Y1 - 2007/7/9
N2 - A new synthetic approach to the bicyclo[3.3.1]nonane system, a common structure in a number of polyisoprenylated phloroglucinol derivatives (phloroglucins), has been developed. The key step in our approach is a 'one-pot' procedure of two successive reactions, the intramolecular cyclopropanation reaction which affords the tricyclo[4.4.0.05,7]dec-2-ene derivative and its methoxy group directed regioselective ring-opening reaction mediated by ZnCl2, producing the desired bicyclo[3.3.1]nonane as the sole product.
AB - A new synthetic approach to the bicyclo[3.3.1]nonane system, a common structure in a number of polyisoprenylated phloroglucinol derivatives (phloroglucins), has been developed. The key step in our approach is a 'one-pot' procedure of two successive reactions, the intramolecular cyclopropanation reaction which affords the tricyclo[4.4.0.05,7]dec-2-ene derivative and its methoxy group directed regioselective ring-opening reaction mediated by ZnCl2, producing the desired bicyclo[3.3.1]nonane as the sole product.
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U2 - 10.1016/j.tetlet.2007.05.041
DO - 10.1016/j.tetlet.2007.05.041
M3 - Article
AN - SCOPUS:34249990396
SN - 0040-4039
VL - 48
SP - 4873
EP - 4877
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 28
ER -