Stereoselective total synthesis of (+)-strictifolione and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one by Prins reaction and olefin cross-metathesis

Prins and olefin cross-metathesis reactions were used as the key steps for the stereoselective total synthesis of (+)-strictifolione and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one. Removal of MOM protecting groups under neutral conditions using CeCl3·7H2O is an attractive addition to the present strategy.

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(2R,4R,6S)-2-[(Benzyloxy)methyl]-4-(methoxymethoxy)-6-phenyltetrahydro-2H-pyranC21H24O4[α]D25=-13 (c 0.3, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,4R,6S)

(2S,4S)-4-(Ethylperoxy)-6-phenylhexane-1,2-diolC14H22O4[α]D25=+41 (c 2.4, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,4S)

(2R)-2-[(2S)-2-(Methoxymethoxy)-4-phenylbutyl]oxetaneC14H20O3[α]D25=+12.3 (c 2.1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R)-2-(2S)

(4R,6S)-6-(Methoxymethoxy)-8-phenyl-1-octyn-4-olC14H22O3[α]D25=+40.7 (c 1.95, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4R,6S)

(4R,6S)-6-(Ethylperoxy)-8-phenyl-1-octen-4-ol (16)C16H24O3[α]D25=+35.5 (c 1.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4R,6S)

(3S)-3-[1-(tert-Butyl)-1,1-dimethylsilyl]oxy-4-penten-1-olC11H24O2Si[α]D25 = +1.9 (c 1.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S)

Methyl (2Z,5S)-5-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-2,6-heptadienoateC14H20O3Si[α]D25=-8.1 (c 0.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2Z,5S)

(6R)-6-[(E,4S,6S)-4,6-Dihydroxy-8-phenyl-1-octenyl]-5,6-dihydro-2H-2-pyranoneC19H24O4[α]D25=+37.8 (c 0.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (6R)-6-[(E,4S,6S)

(6R)-6-Vinyl-5,6-dihydro-2H-2-pyranoneC7H8O2[α]D25=+95.2 (c 0.85, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (6R)

(2R,4R,6R)-2-[(Benzyloxy)methyl]-4-(methoxymethoxy)-6-(4-phenylbutyl)tetrahydro-2H-pyranC24H34O4[α]D25=+5.7 (c 1.02, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,4R,6R)

[(2R,4R,6R)-4-(Methoxymethoxy)-6-(4-phenylbutyl)tetrahydro-2H-2-pyranyl]methanolC18H28O4[α]D25=+3.0 (c 0.32, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,4R,6R)

(2R,4R,6R)-2-[(Benzyloxy)methyl]-6-(4-phenylbutyl)tetrahydro-2H-4-pyranolC23H30O3[α]D=+10.0[α]D=+10.0 (c 1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,4R,6R)

(3R,4E,7R,9R)-7-(Methoxymethoxy)-13-phenyl-1-(tetrahydro-2H-2-pyranyloxy)-4-tridecene-3,9-diolC26H42O6[α]D25=-18.0 (c 1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3R,4E,7R,9R)

(3R,4E,7R,9R)-3,7,9-Tri(methoxymethoxy)-13-phenyl-4-tridecen-1-olC25H42O7[α]D25=+18.5 (c 1.3, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3R,4E,7R,9R)

2-[(3R,4E,7R,9R)-3,7,9-Tri(methoxymethoxy)-13-phenyl-4-tridecenyl]oxytetrahydro-2H-pyranC30H50O8[α]D25=+9.3 (c 1.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3R,4E,7R,9R)

(5R,7R)-7-(Methoxymethoxy)-1-phenyl-9-decen-5-olC18H28O3[α]D25=-30.5 (c 1.4, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (5R,7R)

(6R)-6-[(E,4R,6R)-4,6-Dihydroxy-10-phenyl-1-decenyl]-5,6-dihydro-2H-2-pyranoneC21H28O4[α]D25=+52.5 (c 0.25, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (6R)-6-[(E,4R,6R)

Methyl(2Z,5R,6E,9R,11R)-5,9,11-tri(methoxymethoxy)-15-phenyl-2,6-pentadecadienoateC28H44O8[α]D25=+15.0 (c 1.05, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2Z,5R,6E,9R,11R)

(5R,7R)-7-(Methoxymethoxy)-1-phenyl-9-decen-5-olC18H28O3[α]D25=-30.5 (c 1.4, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (5R,7R)