| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346064 | Tetrahedron: Asymmetry | 2012 | 11 Pages |
A synthetic route to the protected quaternary α-amino acid 2 with a hydroxylated side chain has been achieved. The key transformations are the diastereoselective substrate-controlled epoxidation of allylic alcohol 4; a highly stereoselective oxidation–reduction protocol, and the excellent regioselective isomerization of the oxazolidinone ring to give an oxazinanone skeleton in derivative 3. The carboxylic acid 2 obtained represents the polar substructure, which is present in myriocin 1.
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(3aR,4′S,5S,6aR)-5-(Acetoxymethyl)-3′-benzyl-2,2-dimethyldihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4′-oxazolidin]-2′-oneC19H23NO7[α]D20+123.2 (c 0.21, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (3aR,4′S,5S,6aR)
(5R,6S)-1-Benzyl-6-[(E)-3′-hydroxyprop-1′-enyl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro [4.5]decan-2-oneC18H23NO5[α]D20=+18.9 (c 0.28, CH3OH)Source of chirality: d-glucoseAbsolute configuration: (5R,6S)
(4R)-3-Benzyl-4-[(1′S,2′E)-1′,4′-dihydroxybut-2′-enyl]-4-(hydroxymethyl)oxazolidin-2-oneC15H19NO5[α]D20=+31.1 (c 0.29, CH3OH)Source of chirality: d-glucoseAbsolute configuration: (1′S, 4R)
(5R,6R)-1-Benzyl-6-[(2′S,3′S)-3′-(hydroxymethyl)oxiran-2′-yl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-oneC18H23NO6[α]D20=+79.1 (c 0.18, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (2′S,3′S,5R, 6R)
(4aS,8R,8aR)-5-Benzyl-8-{2′-[(tert-butyldimethylsilyl)oxy]ethyl}-4a-(benzyloxymethyl)-2,2-dimethyltetrahydro-[1,3]dioxino[5,4-d][1,3]oxazin-6(4H)-oneC31H45NO6Si[α]D20=+43.8 (c 0.15, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (4aS,8R,8aR)
(4aS,8R,8aR)-5-Benzyl-8-{2′-[(tert-butyldimethylsilyl)oxy]ethyl}-2,2-dimethyl-6-oxohexahydro-[1,3]dioxino[5,4-d][1,3]oxazin-4a-carboxylic acidC24H37NO7Si[α]D20=+24.3 (c 0.06, CH3OH)Source of chirality: d-glucoseAbsolute configuration: (4aS,8R,8aR)
Methyl (4aS,8R,8aR)-5-Benzyl-8-{2′-[(tert-butyldimethylsilyl)oxy]ethyl}-2,2-dimethyl-6-oxohexahydro-[1,3]dioxino[5,4-d][1,3]oxazin-4a-carboxylateC25H39NO7Si[α]D20=+70.7 (c 0.20, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (4aS,8R,8aR)
