Stereoselective total synthesis of (+)-strictifolione and (6R)-6[(E,4R,6R)-4,6-dihydro-10-phenyl-1-decenyl)-5,6-dihydro-2H-2-pyrone

The stereoselective total synthesis of two naturally occurring α-pyrone derivatives, (+)-strictifolione and (6R)-6[(E,4R,6R)-4,6-dihydroxy-10-phenyl-1-decanyl]-5,6-dihydro-2H-2-pyrone has been accomplished involving the Sharpless kinetic resolution and olefin cross-metathesis as the key reactions.

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(S)-1-((2S,3S)-3-Phenethyloxiran-2-yl)but-3-en-1-olC14H18O2[α]D25=-11.2 (c 1.0, CHCl3)Absolute configuration: (1S,2S,3S)Source of chirality: asymmetric synthesis

(3S,5S)-1-Phenyloct-7-ene-3, 5-diolC14H20O2[α]D25=+4.1 (c 1.0, CHCl3)Absolute configuration: (3S,5S)Source of chirality: asymmetric synthesis

(R)-1-((2R,3R)-3-(4-Phenylbutyl) oxiran-2-yl) but-3-en-1-olC16H22O2[α]D25=+4.8 (c 1.0, CHCl3)Absolute configuration: (1R,2R,3R)Source of chirality: asymmetric synthesis

(4R,6R)-10-Phenyldec-1-ene-4,6-diolC16H24O2[α]D25=-5.75 (c 1.0, CHCl3)Absolute configuration: (4R,6R)Source of chirality: asymmetric synthesis

(R)-Ethyl-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(methylthiocarbonothioyloxy)acetateC11H18O5S2[α]D25=-15.2 (c 1.0, CHCl3)Absolute configuration: (2R,4S)Source of chirality: l-ascorbic acid

(R)-Ethyl-2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetateC9H16O4[α]D25=-11.4 (c 1.0, CHCl3)Absolute configuration: (4R)Source of chirality: l-ascorbic acid

(R,Z)-Methyl-4-(2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoateC10H16O4[α]D25=+1.7 (c 1.0, CHCl3)Absolute configuration: (4R,2Z)Source of chirality: l-ascorbic acid