Abstract
An asymmetric synthesis of the selective C17,20-lyase inhibitor 2 has been established in eight steps from 2,3-dihydroxynaphthalene 9. The key steps are the enantioselective oxidation of ketone 17 to the chiral α-hydroxy ketone 18 and the diastereoselective Grignard reaction of 18 to the (2R,3S)-diol 21. In addition, a simple procedure for the preparation of imidazolyl 1,4-dimagnesium bromide has been established; the Grignard reaction of 11 using this reagent in the presence of cinchonine provided 2 with 44% ee.
| Original language | English |
|---|---|
| Pages (from-to) | 2021-2028 |
| Number of pages | 8 |
| Journal | Tetrahedron Asymmetry |
| Volume | 15 |
| Issue number | 13 |
| DOIs | |
| Publication status | Published - Jul 5 2004 |
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All Science Journal Classification (ASJC) codes
- Catalysis
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
Cite this
Synthetic studies on (1S)-1-(6,7-dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl) -2-methylpropan-1-ol as a selective C17,20-lyase inhibitor. / Matsunaga, Nobuyuki; Kaku, Tomohiro; Ojida, Akio; Tasaka, Akihiro.
In: Tetrahedron Asymmetry, Vol. 15, No. 13, 05.07.2004, p. 2021-2028.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Synthetic studies on (1S)-1-(6,7-dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl) -2-methylpropan-1-ol as a selective C17,20-lyase inhibitor
AU - Matsunaga, Nobuyuki
AU - Kaku, Tomohiro
AU - Ojida, Akio
AU - Tasaka, Akihiro
PY - 2004/7/5
Y1 - 2004/7/5
N2 - An asymmetric synthesis of the selective C17,20-lyase inhibitor 2 has been established in eight steps from 2,3-dihydroxynaphthalene 9. The key steps are the enantioselective oxidation of ketone 17 to the chiral α-hydroxy ketone 18 and the diastereoselective Grignard reaction of 18 to the (2R,3S)-diol 21. In addition, a simple procedure for the preparation of imidazolyl 1,4-dimagnesium bromide has been established; the Grignard reaction of 11 using this reagent in the presence of cinchonine provided 2 with 44% ee.
AB - An asymmetric synthesis of the selective C17,20-lyase inhibitor 2 has been established in eight steps from 2,3-dihydroxynaphthalene 9. The key steps are the enantioselective oxidation of ketone 17 to the chiral α-hydroxy ketone 18 and the diastereoselective Grignard reaction of 18 to the (2R,3S)-diol 21. In addition, a simple procedure for the preparation of imidazolyl 1,4-dimagnesium bromide has been established; the Grignard reaction of 11 using this reagent in the presence of cinchonine provided 2 with 44% ee.
UR - http://www.scopus.com/inward/record.url?scp=3142526440&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=3142526440&partnerID=8YFLogxK
U2 - 10.1016/j.tetasy.2004.05.044
DO - 10.1016/j.tetasy.2004.05.044
M3 - Article
AN - SCOPUS:3142526440
VL - 15
SP - 2021
EP - 2028
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 13
ER -