The reported enzymatic resolution products {acetate of (1
S,4a
S,8a
S)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-
trans-naphthalene-1-methanol-2-ethylene acetal} (8a
S)-5 (>99% ee)] and [(1
R,4a
R,8a
R)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-
trans-naphthalene-1-methanol-2-ethylene acetal (8a
R)-4 (98% ee) were converted to (+)-α-polypodatetraene (1) and methyl (5
R,10
R,13
R)-labda-8-en-15-oate (2), respectively. For the synthesis of (5
R,10
R,13
R)-2, chiral isoprene congener (3
S)-26 corresponding to the right part of 2 was synthesized based on the lipase-assisted resolution of (±)-2-methyl-3- (
p-methoxyphenyl)propanol (17).
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