Stereoselective synthesis towards verbalactone and (+)-(3R,5R)-3-hydroxy-5-decanolide

The stereoselective synthesis towards biologically active verbalactone and (+)-(3R,5R)-3-hydroxy-5-decanolide has been described. The key functionalities are derived from a chiral-auxiliary mediated acetate aldol addition, an oxa-Michael reaction and a 1,3-syn-reduction.

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(R)-1-(4-Benzyl-2-thioxothiazolidin-3-yl)ethanoneC12H13NOS2[α]D25=-210.0 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4R)

(R)-1-(R)-4-Benzyl-2-thioxothiazolidin-3-yl)-3-hydroxyoctan-1-oneC18H25NO2S2[α]D25=-72.6 (c 0.9, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4R,8R)

(S)-1-((R)-4-Benzyl-2-thioxothiazolidin-3-yl)-3-hydroxyoctan-1-oneC18H25NO2S2[α]D25=-118.3 (c 1.08, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4R,8S)

(R,E)-Ethyl 5-hydroxydec-2-enoateC12H22O3[α]D25=-4.5 (c 0.9, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (5R)

Ethyl 2-((2R,4R,6R)-6-pentyl-2-phenyl-1,3-dioxan-4-yl)acetateC19H28O4[α]D25=+85.0 (c 0.9, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,4R,6R)

2-((2R,4R,6R)-6-Pentyl-2-phenyl-1,3-dioxan-4-yl)acetic acidC17H24O4[α]D25=+5.8 (c 0.9, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,4R,6R)

(R)-3-Hydroxy-N-methoxy-N-methyloctanamideC10H21NO3[α]D25=-29.2 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3R)

(R)-6-Hydroxyundec-1-en-4-oneC11H20O2[α]D25=-37.1 (c 0.48, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (6R)

(4S,6R)-Undec-1-ene-4,6-diolC11H22O2[α]D25=+3.4 (c 0.37, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4S,6R)

(2R,4S,6R)-4-Allyl-6-pentyl-2-phenyl-1,3-dioxaneC18H26O2[α]D25=+1.0 (c 0.3, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2R,4S,6R)

(4R,6R)-4-Hydroxy-6-pentyltetrahydro-2H-pyran-2-oneC10H18O3[α]D25=+25.2 (c 0.9, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (4R,6R)