Chemoenzymatic synthesis of (+)-alpha-polypodatetraene and methyl (5R,10R,13R)-labda-8-en-15-oate.
The reported enzymatic resolution products {acetate of (1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal} (8aS)-5 (>99% ee)] and [(1R,4aR,8aR)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal (8aR)-4 (98% ee) were converted to (+)-alpha-polypodatetraene (1) and methyl (5R,10R,13R)-labda-8-en-15-oate (2), respectively. For the synthesis of (5R,10R,13R)-2, chiral isoprene congener (3S)-26 corresponding to the right part of 2 was synthesized based on the lipase-assisted resolution of (+/-)-2-methyl-3- (p-methoxyphenyl)propanol (17).
Kinoshita
Masako
M
School of Pharmaceutical Sciences, Toho University, Chiba, Japan.
Miyake
Takahiro
T
Arima
Yuusuke
Y
Oguma
Minako
M
Akita
Hiroyuki
H
D002384:Catalysis; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure; D011549:Pseudomonas / Q000201:enzymology; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry*
D013729:Terpenes; C525779:methyllabda-8-en-15-oate; C525778:polypodatetraene; D008049:Lipase