Abstract
Simple synthesis of (±)-estrone methyl ether by the conjugate addition-enolate methylation of the 2-alkylcyclopentenone followed by the intramolecular Diels-Alder reaction of the o-quinodimethane, and discussions for the diastereoselectivity in the enolatemethylation based on the MM2 transition structure model are presented.
| Original language | English |
|---|---|
| Pages (from-to) | 4999-5002 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 30 |
| Issue number | 37 |
| DOIs | |
| Publication status | Published - 1989 |
| Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Takahashi, T., Shimizu, K., Doi, T., Tsuji, J., & Yamamoto, K. (1989). Efficient approach to the oppolzer-kametani intermediate for estrone methyl ether using the conjugate addition-enolate methylation of the cyclopentenone containing an α-appended benzocyclobutane moiety. Tetrahedron Letters, 30(37), 4999-5002. https://doi.org/10.1016/S0040-4039(01)80565-7