Abstract
A concise and high yielding synthesis of (-)-tabtoxinine-β-lactam 1, the cause of tobacco wildfire disease, was achieved from l-serine. A concise and high yielding synthesis of (-)-tabtoxinine-β-lactam 1, the cause of tobacco wildfire disease, was achieved from l-serine using a zinc-mediated coupling reaction, Sharpless asymmetric dihydroxylation and lactamization of N-OBn amide as the key steps.
| Original language | English |
|---|---|
| Pages (from-to) | 8191-8194 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 45 |
| Issue number | 44 |
| DOIs | |
| Publication status | Published - Oct 25 2004 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Facile synthesis of (-)-tabtoxinine-β-lactam and its (3′R)-isomer. / Kiyota, Hiromasa; Takai, Takafumi; Saitoh, Masatoshi; Nakayama, Osamu; Oritani, Takayuki; Kuwahara, Shigefumi.
In: Tetrahedron Letters, Vol. 45, No. 44, 25.10.2004, p. 8191-8194.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Facile synthesis of (-)-tabtoxinine-β-lactam and its (3′R)-isomer
AU - Kiyota, Hiromasa
AU - Takai, Takafumi
AU - Saitoh, Masatoshi
AU - Nakayama, Osamu
AU - Oritani, Takayuki
AU - Kuwahara, Shigefumi
PY - 2004/10/25
Y1 - 2004/10/25
N2 - A concise and high yielding synthesis of (-)-tabtoxinine-β-lactam 1, the cause of tobacco wildfire disease, was achieved from l-serine. A concise and high yielding synthesis of (-)-tabtoxinine-β-lactam 1, the cause of tobacco wildfire disease, was achieved from l-serine using a zinc-mediated coupling reaction, Sharpless asymmetric dihydroxylation and lactamization of N-OBn amide as the key steps.
AB - A concise and high yielding synthesis of (-)-tabtoxinine-β-lactam 1, the cause of tobacco wildfire disease, was achieved from l-serine. A concise and high yielding synthesis of (-)-tabtoxinine-β-lactam 1, the cause of tobacco wildfire disease, was achieved from l-serine using a zinc-mediated coupling reaction, Sharpless asymmetric dihydroxylation and lactamization of N-OBn amide as the key steps.
UR - http://www.scopus.com/inward/record.url?scp=4744344729&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=4744344729&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2004.09.033
DO - 10.1016/j.tetlet.2004.09.033
M3 - Article
AN - SCOPUS:4744344729
VL - 45
SP - 8191
EP - 8194
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 44
ER -