TY - JOUR
T1 - Toward the synthesis of γ-pyrone-containing natural products
T2 - Diastereoselective aldol-type reaction of a γ-pyrone
AU - Takemura, Takuma
AU - Hayakawa, Ichiro
AU - Fukasawa, Emi
AU - Sengoku, Tetsuya
AU - Kigoshi, Hideo
N1 - Funding Information:
This work was supported by Grants-in-Aid for Scientific Research, from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan ; by a grant from the Uehara Memorial Foundation (H.K.); and by a grant from the University of Tsukuba , Strategic Initiatives (A), Center for Creation of Functional Materials (CCFM). We would like to thank Professors Akira Sekiguchi and Masaaki Ichinohe (University of Tsukuba) for the X-ray crystallographic analysis and for their helpful discussion. I.H. thanks Meiji Seika Award in Synthetic Organic Chemistry, Japan and the Suntory Institute for Bioorganic Research (SUNBOR GRANT) for financial support.
PY - 2012/8/12
Y1 - 2012/8/12
N2 - The diastereoselective aldol-type reaction of a γ-pyrone via a sodium anion has been developed. This reaction is useful for synthesizing γ-pyrone-containing natural products. Also, we applied the Mukaiyama aldol-type reaction of silyl enol ether of γ-pyrone by using TiCl 4. This Mukaiyama aldol-type reaction of γ-pyrone indicated higher anti-aldol selectivity than the aldol-type reaction of a γ-pyrone with NaHMDS.
AB - The diastereoselective aldol-type reaction of a γ-pyrone via a sodium anion has been developed. This reaction is useful for synthesizing γ-pyrone-containing natural products. Also, we applied the Mukaiyama aldol-type reaction of silyl enol ether of γ-pyrone by using TiCl 4. This Mukaiyama aldol-type reaction of γ-pyrone indicated higher anti-aldol selectivity than the aldol-type reaction of a γ-pyrone with NaHMDS.
KW - Diastereoselective aldol-type reaction of a γ-pyrone
KW - Mukaiyama aldol-type reaction of a γ-pyrone
KW - anti-Aldol selectivity
UR - http://www.scopus.com/inward/record.url?scp=84862756302&partnerID=8YFLogxK
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U2 - 10.1016/j.tet.2012.05.111
DO - 10.1016/j.tet.2012.05.111
M3 - Article
AN - SCOPUS:84862756302
VL - 68
SP - 6477
EP - 6484
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 32
ER -