TY - JOUR
T1 - Total synthesis of brevetoxin B
AU - Kadota, Isao
AU - Takamura, Hiroyoshi
N1 - Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2007/5
Y1 - 2007/5
N2 - Brevetoxin B was isolated from the red tide organism Karenia brevis in 1981 as the first example of marine polycyclic ethers. This compound shows potent neurotoxicity, by binding to sodium channels, causing massive fish kills and human health problems. Since further biological studies are hampered by the limited availability from nature, chemical synthesis has been the sole realistic way to obtain sufficient amounts of brevetoxin B. Moreover, the huge molecular architecture is a particularly attractive target for synthetic chemists. In this account, we describe the highly convergent total synthesis of brevetoxin B based on our methodology, including intramolecular allylation and subsequent ring-closing metathesis.
AB - Brevetoxin B was isolated from the red tide organism Karenia brevis in 1981 as the first example of marine polycyclic ethers. This compound shows potent neurotoxicity, by binding to sodium channels, causing massive fish kills and human health problems. Since further biological studies are hampered by the limited availability from nature, chemical synthesis has been the sole realistic way to obtain sufficient amounts of brevetoxin B. Moreover, the huge molecular architecture is a particularly attractive target for synthetic chemists. In this account, we describe the highly convergent total synthesis of brevetoxin B based on our methodology, including intramolecular allylation and subsequent ring-closing metathesis.
KW - Brevetoxin B
KW - Intramolecular allylation
KW - Polycyclic ethers
KW - Ring-closing metathesis
KW - Total synthesis
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U2 - 10.5059/yukigoseikyokaishi.65.430
DO - 10.5059/yukigoseikyokaishi.65.430
M3 - Article
AN - SCOPUS:34547489551
VL - 65
SP - 430
EP - 437
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
SN - 0037-9980
IS - 5
ER -