Synthesis of myo-inositol derivatives required for the total synthesis of surugatoxin, prosurugatoxin, and neosurugatoxin.
Two myo-inositol derivatives (4) and (5), required for the total synthesis of surugatoxin, prosurugatoxin, and neosurugatoxin, were prepared. Synthesis of (+/-)-2,3-O-cyclohexylidene-4,5-O-isopropylidene-1-O-methoxymethyl-myo-i nositol (4) was achieved from (+/-)-1-O-benzoyl-2,3-O-cyclohexylidene-4,5-O-isopropylidene-myo-inosito l (6) in 4 steps, and (-)-2,3-O-cyclohexylidene-1,4-di-O-methoxymethyl-5-O-[2',3',4'-tri-O-ace tyl- beta-D-xylopyranosyl]-myo-inositol (5) was synthesized from (+/-)-1-O-benzoyl-2,3-O-cyclohexylidene-5,6-O-isopropylidene-myo-inosito l (12) in 7 steps.
Okada
K
K
Hashizume
K
K
Tanino
H
H
Kakoi
H
H
Inoue
S
S
D055598:Chemical Phenomena; D002621:Chemistry; D007294:Inositol / Q000138:chemical synthesis* / Q000494:pharmacology; D008978:Mollusk Venoms / Q000138:chemical synthesis*
D008978:Mollusk Venoms; C010340:surugatoxin; D007294:Inositol; C036793:neosurugatoxin; C047839:prosurugatoxin