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• W2020017719 abstract "14,15-dinor-17-acetoxy-7-labden-13-one, 4 was prepared from zamoranic acid methyl ester 5. Photochemical cleavage of 4 gave 12-acetoxy-7,9(11)-drimadiene, 3, in 75% overall yield. The chemo- and diastereoselective epoxidation of 3 afforded 12-acetoxy-9α and 9β(11)-epoxy-7-drimene, 17 and 18 in 4:1 ratio. Ring-opening of 17 (or the mixture 1718) using BF3·Et2O or ring-opening of the mixture 1718 lead to the synthetic precursor of polygodial: (9R)-12-acetoxy-drimen-11-al, 20, with a 90% diastereoisomeric excess. The chemo- and diastereoselective cis-hydroxylation of diene 3 led to the synthetic precursor of warburganal 9α,11,12-trihydroxy-7-drimene, 29 with 47% yield. Polygodial and warburganal were prepared from zamoranic acid methyl ester in 55 and 27% overall yield, respectively." @default.
• W2020017719 created "2016-06-24" @default.
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• W2020017719 date "1995-02-01" @default.
• W2020017719 modified "2023-10-01" @default.
• W2020017719 title "Chemistry of zamoranic acid. Part IX homochiral synthesis of polygodial and warburganal from 17-acetoxy-7-labden-15-ol" @default.
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• W2020017719 doi "https://doi.org/10.1016/0040-4020(94)01061-4" @default.
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