Abstract
The total synthesis of palytoxin carboxylic acid and palytoxin amide was achieved from the fully protected palytoxin carboxylic acid. The fully protected palytoxin carboxylic acid 1 contains eight different and 42 total protecting groups. All these protecting groups were successfully removed in five synthetic operations, i.e., (1) DDQ treatment, (2) aqueous HClO4 hydrolysis, (3) aqueous LiOH hydrolysis, (4) (n-Bu)4NF treatment, and (5) aqueous AcOH hydrolysis. The completely deprotected palytoxin carboxylic acid was isolated in approximately 35% overall yield and identified with the authentic sample. An efficient method to convert palytoxin carboxylic acid 2 into palytoxin amide 3 was developed.
| Original language | English |
|---|---|
| Pages (from-to) | 7530-7533 |
| Number of pages | 4 |
| Journal | Journal of the American Chemical Society |
| Volume | 111 |
| Issue number | 19 |
| Publication status | Published - 1989 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Chemistry(all)
Cite this
Total synthesis of palytoxin carboxylic acid and palytoxin amide. / Armstrong, Robert W.; Beau, Jean Marie; Cheon, Seung Hoon; Christ, William J.; Fujioka, Hiromichi; Ham, Won Hun; Hawkins, Lynn D.; Jin, Haolun; Kang, Sung Ho; Kishi, Yoshito; Martinelli, Michael J.; McWhorter, William W.; Mizuno, Masanori; Nakata, Masaya; Stutz, Arnold E.; Talamas, Francisco X.; Taniguchi, Mikio; Tino, Joseph A.; Ueda, Katsuhiro; Uenishi, Jun Ichi; White, James B.; Yonaga, Masahiro.
In: Journal of the American Chemical Society, Vol. 111, No. 19, 1989, p. 7530-7533.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Total synthesis of palytoxin carboxylic acid and palytoxin amide
AU - Armstrong, Robert W.
AU - Beau, Jean Marie
AU - Cheon, Seung Hoon
AU - Christ, William J.
AU - Fujioka, Hiromichi
AU - Ham, Won Hun
AU - Hawkins, Lynn D.
AU - Jin, Haolun
AU - Kang, Sung Ho
AU - Kishi, Yoshito
AU - Martinelli, Michael J.
AU - McWhorter, William W.
AU - Mizuno, Masanori
AU - Nakata, Masaya
AU - Stutz, Arnold E.
AU - Talamas, Francisco X.
AU - Taniguchi, Mikio
AU - Tino, Joseph A.
AU - Ueda, Katsuhiro
AU - Uenishi, Jun Ichi
AU - White, James B.
AU - Yonaga, Masahiro
PY - 1989
Y1 - 1989
N2 - The total synthesis of palytoxin carboxylic acid and palytoxin amide was achieved from the fully protected palytoxin carboxylic acid. The fully protected palytoxin carboxylic acid 1 contains eight different and 42 total protecting groups. All these protecting groups were successfully removed in five synthetic operations, i.e., (1) DDQ treatment, (2) aqueous HClO4 hydrolysis, (3) aqueous LiOH hydrolysis, (4) (n-Bu)4NF treatment, and (5) aqueous AcOH hydrolysis. The completely deprotected palytoxin carboxylic acid was isolated in approximately 35% overall yield and identified with the authentic sample. An efficient method to convert palytoxin carboxylic acid 2 into palytoxin amide 3 was developed.
AB - The total synthesis of palytoxin carboxylic acid and palytoxin amide was achieved from the fully protected palytoxin carboxylic acid. The fully protected palytoxin carboxylic acid 1 contains eight different and 42 total protecting groups. All these protecting groups were successfully removed in five synthetic operations, i.e., (1) DDQ treatment, (2) aqueous HClO4 hydrolysis, (3) aqueous LiOH hydrolysis, (4) (n-Bu)4NF treatment, and (5) aqueous AcOH hydrolysis. The completely deprotected palytoxin carboxylic acid was isolated in approximately 35% overall yield and identified with the authentic sample. An efficient method to convert palytoxin carboxylic acid 2 into palytoxin amide 3 was developed.
UR - http://www.scopus.com/inward/record.url?scp=0000991371&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0000991371&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0000991371
VL - 111
SP - 7530
EP - 7533
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 19
ER -