Abstract
We have developed an efficient construction of spiro derivatives by anodic oxidation of the corresponding phenols, which enabled synthesis of spiroisoxazoline natural products as well as heliannuols, carrying chroman and benzooxepin structures. In addition to nucleophilic attack of hydroxyl or amino groups to the cation generated electrochemerically, it might be of interest to use a carbonyl oxygen as a nucleophilic center, which would provide hemiacetal-type spiro compounds. Gymnastatin A 1 was isolated from the strain of Gymnescella dankaliensis separated from the sponge Halichondria japonica, together with other gymnastatins. This marine natural product consists of the spiro structure between the dienone part including two chlorine atoms, and the tetrahydrofuran ring with a hemiacetal moiety, along with the fatty acid part having an asymmetric carbon center attached with the amino group. As part of our extensive electrochemical investigation of halogenated tyrosine derivatives, synthesis of the acetal-spiro derivatives and its application to gymnastatin A 1 was undertaken to develop further efficient and green sustainable methodology. In these investigations, construction of spiro compounds having hemiacetal moiety, and synthesis of gymnastatin A 1 was achieved successfully. In addition to the synthesis, biological assessment of synthetic samples was examined. Among them, 3, 5, 14, and 15 showed a wide range of inhibitory activity against Gram-positive, -negative bacteria, fungus, and Mycobacterium.
| Original language | English |
|---|---|
| Pages (from-to) | 175-183 |
| Number of pages | 9 |
| Journal | Science and Technology of Advanced Materials |
| Volume | 7 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 2006 Mar |
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Keywords
- Anodic oxidation
- Antimicrobial agents
- Electrochemical synthesis
- Spiro compounds
- Total synthesis
ASJC Scopus subject areas
- Materials Science(all)
Cite this
Synthesis and biological assessment of hemiacetal spiro derivatives towards development of efficient chemotherapeutic agent. / Ogamino, Takahisa; Ohnishi, Sayo; Ishikawa, Yuichi; Sugai, Takeshi; Obata, Rika; Nishiyama, Shigeru.
In: Science and Technology of Advanced Materials, Vol. 7, No. 2, 03.2006, p. 175-183.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and biological assessment of hemiacetal spiro derivatives towards development of efficient chemotherapeutic agent
AU - Ogamino, Takahisa
AU - Ohnishi, Sayo
AU - Ishikawa, Yuichi
AU - Sugai, Takeshi
AU - Obata, Rika
AU - Nishiyama, Shigeru
PY - 2006/3
Y1 - 2006/3
N2 - We have developed an efficient construction of spiro derivatives by anodic oxidation of the corresponding phenols, which enabled synthesis of spiroisoxazoline natural products as well as heliannuols, carrying chroman and benzooxepin structures. In addition to nucleophilic attack of hydroxyl or amino groups to the cation generated electrochemerically, it might be of interest to use a carbonyl oxygen as a nucleophilic center, which would provide hemiacetal-type spiro compounds. Gymnastatin A 1 was isolated from the strain of Gymnescella dankaliensis separated from the sponge Halichondria japonica, together with other gymnastatins. This marine natural product consists of the spiro structure between the dienone part including two chlorine atoms, and the tetrahydrofuran ring with a hemiacetal moiety, along with the fatty acid part having an asymmetric carbon center attached with the amino group. As part of our extensive electrochemical investigation of halogenated tyrosine derivatives, synthesis of the acetal-spiro derivatives and its application to gymnastatin A 1 was undertaken to develop further efficient and green sustainable methodology. In these investigations, construction of spiro compounds having hemiacetal moiety, and synthesis of gymnastatin A 1 was achieved successfully. In addition to the synthesis, biological assessment of synthetic samples was examined. Among them, 3, 5, 14, and 15 showed a wide range of inhibitory activity against Gram-positive, -negative bacteria, fungus, and Mycobacterium.
AB - We have developed an efficient construction of spiro derivatives by anodic oxidation of the corresponding phenols, which enabled synthesis of spiroisoxazoline natural products as well as heliannuols, carrying chroman and benzooxepin structures. In addition to nucleophilic attack of hydroxyl or amino groups to the cation generated electrochemerically, it might be of interest to use a carbonyl oxygen as a nucleophilic center, which would provide hemiacetal-type spiro compounds. Gymnastatin A 1 was isolated from the strain of Gymnescella dankaliensis separated from the sponge Halichondria japonica, together with other gymnastatins. This marine natural product consists of the spiro structure between the dienone part including two chlorine atoms, and the tetrahydrofuran ring with a hemiacetal moiety, along with the fatty acid part having an asymmetric carbon center attached with the amino group. As part of our extensive electrochemical investigation of halogenated tyrosine derivatives, synthesis of the acetal-spiro derivatives and its application to gymnastatin A 1 was undertaken to develop further efficient and green sustainable methodology. In these investigations, construction of spiro compounds having hemiacetal moiety, and synthesis of gymnastatin A 1 was achieved successfully. In addition to the synthesis, biological assessment of synthetic samples was examined. Among them, 3, 5, 14, and 15 showed a wide range of inhibitory activity against Gram-positive, -negative bacteria, fungus, and Mycobacterium.
KW - Anodic oxidation
KW - Antimicrobial agents
KW - Electrochemical synthesis
KW - Spiro compounds
KW - Total synthesis
UR - http://www.scopus.com/inward/record.url?scp=33645872131&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33645872131&partnerID=8YFLogxK
U2 - 10.1016/j.stam.2005.10.004
DO - 10.1016/j.stam.2005.10.004
M3 - Article
AN - SCOPUS:33645872131
VL - 7
SP - 175
EP - 183
JO - Science and Technology of Advanced Materials
JF - Science and Technology of Advanced Materials
SN - 1468-6996
IS - 2
ER -