Abstract
The novel monocyclic dienediyne 2, which is a simplified analogue of the neocarzinostatin chromophore (1), was synthesized from D-xylitol via conversion of the keto-aldehyde 13 into the highly strained 10-membered ring compound 14 by a simple intramolecular aldol condensation as the key step. The mode of cycloaromatization of 2 by a thiol addition, reminiscent of the chemistry of 1, was also demonstrated.
| Original language | English |
|---|---|
| Pages (from-to) | 1573-1576 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 35 |
| Issue number | 10 |
| DOIs | |
| Publication status | Published - 1994 Mar 7 |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
A novel monocyclic dienediyne system : Synthesis and mode of aromatization. / Toshima, Kazunobu; Yanagawa, Koji; Ohta, Kazumi; Kano, Takaaki; Nakata, Masaya.
In: Tetrahedron Letters, Vol. 35, No. 10, 07.03.1994, p. 1573-1576.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - A novel monocyclic dienediyne system
T2 - Synthesis and mode of aromatization
AU - Toshima, Kazunobu
AU - Yanagawa, Koji
AU - Ohta, Kazumi
AU - Kano, Takaaki
AU - Nakata, Masaya
PY - 1994/3/7
Y1 - 1994/3/7
N2 - The novel monocyclic dienediyne 2, which is a simplified analogue of the neocarzinostatin chromophore (1), was synthesized from D-xylitol via conversion of the keto-aldehyde 13 into the highly strained 10-membered ring compound 14 by a simple intramolecular aldol condensation as the key step. The mode of cycloaromatization of 2 by a thiol addition, reminiscent of the chemistry of 1, was also demonstrated.
AB - The novel monocyclic dienediyne 2, which is a simplified analogue of the neocarzinostatin chromophore (1), was synthesized from D-xylitol via conversion of the keto-aldehyde 13 into the highly strained 10-membered ring compound 14 by a simple intramolecular aldol condensation as the key step. The mode of cycloaromatization of 2 by a thiol addition, reminiscent of the chemistry of 1, was also demonstrated.
UR - http://www.scopus.com/inward/record.url?scp=0028293542&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0028293542&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(00)76761-X
DO - 10.1016/S0040-4039(00)76761-X
M3 - Article
AN - SCOPUS:0028293542
VL - 35
SP - 1573
EP - 1576
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 10
ER -