Abstract
The diastereoselective cyclization of 2a to 5a, which was employed in our novel synthesis of dl-griseofulvin (7a), was studied in detail. It was found that the use of the metallic bases resulted in excellent diastereoselectively, whereas organic bases are ineffective for diastereoselective cyclization. Consequently, diastereoselective cyclization of 2 to 5 was proposed to proceed through the intramolecular Michael reaction under chelation control.
| Original language | English |
|---|---|
| Pages (from-to) | 3048-3050 |
| Number of pages | 3 |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 39 |
| Issue number | 11 |
| Publication status | Published - 1991 |
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ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
- Drug Discovery
- Pharmacology
Cite this
Intramolecular Michael reaction in diastereoselective synthesis of dl-Griseofulvin. / Takeuchi, Yasuo; Watanabe, I.; Tomozane, H.; Hashigaki, K.; Yamato, M.
In: Chemical and Pharmaceutical Bulletin, Vol. 39, No. 11, 1991, p. 3048-3050.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Intramolecular Michael reaction in diastereoselective synthesis of dl-Griseofulvin
AU - Takeuchi, Yasuo
AU - Watanabe, I.
AU - Tomozane, H.
AU - Hashigaki, K.
AU - Yamato, M.
PY - 1991
Y1 - 1991
N2 - The diastereoselective cyclization of 2a to 5a, which was employed in our novel synthesis of dl-griseofulvin (7a), was studied in detail. It was found that the use of the metallic bases resulted in excellent diastereoselectively, whereas organic bases are ineffective for diastereoselective cyclization. Consequently, diastereoselective cyclization of 2 to 5 was proposed to proceed through the intramolecular Michael reaction under chelation control.
AB - The diastereoselective cyclization of 2a to 5a, which was employed in our novel synthesis of dl-griseofulvin (7a), was studied in detail. It was found that the use of the metallic bases resulted in excellent diastereoselectively, whereas organic bases are ineffective for diastereoselective cyclization. Consequently, diastereoselective cyclization of 2 to 5 was proposed to proceed through the intramolecular Michael reaction under chelation control.
UR - http://www.scopus.com/inward/record.url?scp=0026328725&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0026328725&partnerID=8YFLogxK
M3 - Article
VL - 39
SP - 3048
EP - 3050
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
SN - 0009-2363
IS - 11
ER -