| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1350556 | Tetrahedron: Asymmetry | 2007 | 6 Pages |
The synthesis of a C1–C14 fragment of a marine cytotoxic natural product Palmerolide A is described. The key steps involved in this synthesis are deoxygenative rearrangement of an alkynol followed by an asymmetric dihydroxylation of a diene ester and CBS-reduction.
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(4S,5S,2E)-Ethyl-8-(benzyloxy)-4,5-dihydroxyoct-2-enoateC17H24O5[α]D25=-12.2 (c 5.7, CHCl3)Source of chirality: ADmix-αAbsolute configuration: (4S,5S,2E)
(E)-Ethyl 3-((4S,5S)-5-(3-(benzyloxy)propyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylateC20H28O5[α]D25=-14.5 (c 4.6, CHCl3)Source of chirality: ADmix-αAbsolute configuration: (4S,5S,E)
(E)-3-((4S,5S)-5-(3-(Benzyloxy)propyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-olC18H26O4[α]D25=-6.3 (c 3.15, CHCl3)Source of chirality: ADmix-αAbsolute configuration: (4S,5S,E)
(E)-3-((4S,5S)-5-(3-(Benzyloxy)propyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylaldehydeC18H24O4[α]D25=-13.1 (c 0.7, CHCl3)Source of chirality: ADmix-αAbsolute configuration: (4S,5S,E)
(E)-1-((4S,5S)-5-(3-(Benzyloxy)-propyl)-2,2-dimethyl-1,3-dioxolan-4-yl)hepta-1,6-diene-3-oneC22H30O4[α]D25=-11.9 (c 5.1, CHCl3)Source of chirality: ADmix-αAbsolute configuration: (4S,5S,E)
(S,E)-1-((4S,5S)-5-(3-(Benzyloxy)propyl)-2,2-dimethyl-1,3-dioxolan-4-yl)hepta-1,6-dien-3-olC22H32O4[α]D25=-46.95 (c 1.45, CHCl3)Source of chirality: ADmix-α, CBS-reductionAbsolute configuration: (4S,5S,S,E)
((S,E)-1-((4S,5S)-5-(3-(Benzyloxy)propyl)-2,2-dimethyl-1,3-dioxolan-4-yl)hepta-1,6-dien-3-yloxy)(tert-butyl)dimethylsilaneC28H46O4Si[α]D25=-6.5 (c 1.3, CHCl3)Source of chirality: ADmix-α, CBS-reductionAbsolute configuration: (4S,5S,S,E)
(S,E)-7-((4S,5S)-5-(3-(Benzyloxy)propyl)-2,2-dimethyl-1,3-dioxolan-4yl)-5-(tert-butyl dimethyl silyloxy)hept-6-en-1-olC28H48NO5Si[α]D25=-79.7 (c 0.9 CHCl3)Source of chirality: ADmix-α, CBS-reductionAbsolute configuration: (4S,5S,S,E)
(S,2E,8E)-Methyl 9-((4S,5S),-5-(3-(benzyloxy)propyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7-(tert-butyldimethylsilyloxy)nona-2,8-dienoateC31H50O6Si[α]D25=-29.6 (c 2.85, CHCl3)Source of chirality: ADmix-α, CBS-reductionAbsolute configuration: (S,2E,8E) (4S,5S)
