A stereoselective synthesis of the C10-C31 (BCDEF ring) portion of pinnatoxin A.
[reaction: see text] An efficient synthesis of the C10-C31 (BCDEF ring) portion of pinnatoxin A has been achieved. The key step is a highly stereoselective construction of the dispiroketal (BCD ring) system employing an intramolecular hetero-Michael reaction of a reversibly formed hemiketal alkoxide through the use of LiOMe.
Nakamura
S
S
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
Inagaki
J
J
Sugimoto
T
T
Kudo
M
M
Nakajima
M
M
Hashimoto
S
S
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D018360:Crystallography, X-Ray; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D008974:Mollusca / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D008387:Marine Toxins; D013141:Spiro Compounds; C447983:pinnatoxin A