| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1349368 | Tetrahedron: Asymmetry | 2009 | 5 Pages |
A simple convergent approach towards the total synthesis of bioactive spiroacetals aculeatins A and B is described. The key features of the synthetic strategy include a syn-stereoselective 1,3-asymmetric reduction, epoxide ring opening and oxidative spirocyclization reaction by employing (S)-malic acid as the starting material.
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(2S,4S)-4-(Benzyloxy)-6-heptene-1,2-diolC14H20O3[α]D25=+77.5 (c 1.1, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (2S,4S)
(2S)-2-[(2S)-2-(benzyloxy)-4-pentenyl]oxiraneC14H18O2[α]D25=+25.5 (c 1.1, CHCl3)Source of chirality: (S)-malic acid
(4S,6R)-4-(benzyloxy)-1-nonadecen-6-olC26H44O2[α]D25=+53.5 (c 1.1, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (4S,6R)
[(1R,3S)-3-(Benzyloxy)-1-tridecyl-5-hexenyl]oxy(tert-butyl)dimethylsilaneC32H58O2Si[α]D25=+14.5 (c 1.1, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (1R,3S)
(5S,7R)-5-(Benzyloxy)-1-[4-(benzyloxy)phenyl]-7-[1-(tert-butyl)-1,1dimethylsilyl]oxy-1-icosyn-3-olC46H68O4Si[α]D25=-39.5 (c 1.1, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (5S,7R)
(5R,7R)-5-(Benzyloxy)-1-[4-(benzyloxy)phenyl]-7-[1-(tert-butyl)-1,1 dimethylsilyl]oxy-1-icosyn-3-oneC46H66O4Si[α]D25=+4.5 (c 1.1, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (5R,7R)
(5R,7R)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-5-hydroxy-1-(4-hydroxyphenyl)icosan-3-oneC32H58O4Si[α]D25=-4.5 (c 1.1, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (5R,7R)
Aculeatin AC26H42O4[α]D25=-5.3 (c 1.1, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (2R,4R,6R)
Aculeatin BC26H42O4[α]D25=+53.5 (c 1.1, CHCl3)Source of chirality: (S)-malic acidAbsolute configuration: (2R,4R,6S)
