Highly Z selective synthesis of functionalized monoterpenoids via N-ylide [2,3]sigmatropic rearrangement and its application to 13-cis-retinol

DOI: 10.1246/cl.1996.671

Source and publish data:

Chemistry Letters p. 671 - 672 (1996)

Update date:2022-08-03

Topics:

Authors:

Honda, Kiyoshi

Yoshii, Ichiro

Inoue, Seiichi

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Article abstract of DOI:10.1246/cl.1996.671

Highly stereoselective elongation of a functionalized E isoprene unit on the Z terminal methyl of prenol was achieved by the N-ylide rearrangement of N-tiglyl-β-methallyldimethyl-ammonium salt. (E,Z)-Rearrangement product was converted into 13-cis-retinol via useful conjugated triene isoprenoid synthon.

Full text of DOI:10.1246/cl.1996.671

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