Stereoselective construction of a beta-isopropenyl alcohol moiety at the C(2) and (3) of kallolide A and pinnatin a using a [2,3] Wittig rearrangement of cyclic furfuryl ethers.
A stereocontrolled synthesis of anti- and syn-beta-isopropenyl alcohol moieties at the C(2)-C(3) positions of kallolide A and pinnatin A was accomplished employing the [2,3] Wittig rearrangement of (E)-and (Z)-cyclic furfuryl ethers 8. Enantioselective Wittig rearrangement of (E)- and (Z)-furfuryl ethers 8 using butyllithium and a chiral bis(oxazoline) was also examined to provide (2R,3R)-homoallylic alcohol anti-9 in up to 61% ee and (2R,3S)-syn-9 in up to 93% ee, respectively.
Tsubuki
Masayoshi
M
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan tsubuki@hoshi.ac.jp
Takahashi
Kazunori
K
Honda
Toshio
T
D004224:Diterpenes / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004224:Diterpenes; D004988:Ethers, Cyclic; D005663:Furans; D020005:Propanols