| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344507 | Tetrahedron: Asymmetry | 2011 | 6 Pages |
A brief and facile synthesis of the title compound has been developed using cyclohexylideneglyceraldehyde as a chiral template. The key steps in the synthesis were: (i) two highly diastereoselective organometallic addition reactions to the aldehyde to furnish the required synthons with the appropriate stereogenic centers, and (ii) their cross metathesis to give the E-olefin geometry of the target compound.
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(2R,3S)-1,2-Cyclohexylidenedioxyhex-5-en-3-olC12H20O3[α]D23=+4.9 (c 1.18, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (2R,3S)
(2R,3S)-3-tert-Butyldiphenylsilyloxy-1,2-cyclohexylidenedioxyhex-5-eneC28H38O3Si[α]D24=+16.8 (c 1.13, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (2R,3S)
(4S,5R)-4-tert-Butyldiphenylsilyloxy-5,6-cyclohexylidenedioxyhexan-1olC28H40O4Si[α]D25=+3.4 (c 1.13, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (4S,5R)
(4S,5R)-4-tert-Butyldiphenylsilyloxy-5,6-cyclohexylidenedioxyhexanalC28H38O4Si[α]D24=+7.7 (c 1.24, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (4S,5R)
Ethyl (6S,7R)-6-tert-Butyldiphenylsilyloxy-7,8-cyclohexylidenedioxyoct-2E-enoateC32H44O5Si[α]D24=+12.7 (c 1.07, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (6S,7R)
Ethyl (6S,7R)-6-tert-Butyldiphenylsilyloxy-7,8-cyclohexylidenedioxyoctanoateC32H46O5Si[α]D24=+7.7 (c 1.06, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (6S,7R)
Ethyl (6S,7R)-6-tert-Butyldiphenylsilyloxy-7,8-dihydroxyoctanoateC26H38O5Si[α]D25=+26.5 (c 1.08, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (6S,7R)
Ethyl (6S)-6-tert-Butyldiphenylsilyloxyoct-7-enoateC26H36O3Si[α]D24=+21.3 (c 1.01, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (6S)
(2R,3S)-1,2-Cyclohexylidenedioxyundecan-3-olC17H32O3[α]D24=+12.6 (c 1.02, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (2R,3S)
(2R,3S)-3-tert-Butyldiphenylsilyloxy-1,2-cyclohexylidenedioxyundecaneC33H50O3Si[α]D24=+15.5 (c 1.06, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (2R,3S)
(2R,3S)-3-tert-Butyldiphenylsilyloxyundecane-1,2-diolC27H42O3Si[α]D24=+21.0 (c 1.04, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (2R,3S)
(2R,3S)-3-tert-Butyldiphenylsilyloxy-1,2-epoxyundecaneC27H40O2Si[α]D24=+20.2 (c 1.14, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (2R,3S)
(3R,4S)-4-tert-Butyldiphenylsilyloxydodec-1-en-3-olC28H42O2Si[α]D24=+16.5 (c 1.08, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (3R,4S)
Ethyl (6S,9R,10S)-6,10-di-tert-butyldiphenylsilyloxy-9-hydroxy-octadeca-7E-enoateC52H74O5Si2[α]D25=+16.3 (c 1.02, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (6S,9R,10S)
Ethyl (6S,9R,10S)-6,9,10-trihydroxy-octadeca-7E-enoateC20H38O5[α]D24=+3.3 (c 1.22, CHCl3)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (6S,9R,10S)
(6S,9R,10S)-6,9,10-Trihydroxy-octadeca-7E-enoic acidC18H34O5[α]D24=+6.3 (c 0.980, MeOH)Source of chirality: (R)-cyclohexylideneglyceraldehydeAbsolute configuration: (6S,9R,10S)
