| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345900 | Tetrahedron: Asymmetry | 2013 | 10 Pages |
A short and simple route to the synthesis of pentadec-1-en-4-ol, an important synthetic building block for the aculeatins F and epi-F, insect pheromone 5-hexadecanolide, solenopsin and various other natural products has been developed via proline-catalyzed α-aminoxylation of an aldehyde and hydrolytic kinetic resolution of a terminal epoxide. While the synthesis of aculeatins F and epi-F has been accomplished using a PIFA promoted oxidative spirocyclization/dithiane deprotection reaction sequence and linchpin coupling as key steps, the synthesis of hexadecanolide and a formal synthesis of solenopsin was performed using ring-closing metathesis (RCM) as key step.
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(R)-2-UndecyloxiraneC13H26O[α]D25=+11.5 (c 1.1, THF)Source of chirality: hydrolytic kinetic resolution and l-proline catalyze α-aminoxylationAbsolute configuration: (2R)
(R)-Pentadec-1-en-4-olC15H30O[α]D25=+5.5 (c 1.0, CHCl3)Source of chirality: hydrolytic kinetic resolution and l-proline catalyze α-aminoxylationAbsolute configuration: (4R)
tert-Butyldimethyl(((R)-1-((R)-oxiran-2-yl)tridecan-2-yl)oxy)silaneC21H44O2Si[α]D25=-8.4 (c 1.0, CHCl3)Source of chirality: hydrolytic kinetic resolutionAbsolute configuration: (R,R)
(R)-Tridecane-1,2-diolC13H28O2[α]D25=+10.0 (c 1.00, MeOH)Source of chirality: l-Proline catalyze aminoxylationAbsolute configuration: (1R)
(R)-2-Hydroxytridecyl 4-methylbenzenesulfonateC20H34O4S[α]D25=-9.8 (c 1, CHCl3)Source of chirality: l-Proline catalyze α-aminoxylationAbsolute configuration: (2R)
(R)-2-(Tosyloxy)tridecyl benzoateC27H38O5S[α]D25=-6.9 (c 1.1, CHCl3)Source of chirality: l-Proline catalyze α-aminoxylationAbsolute configuration: (2R)
(2R,4R,6R)-4-Hydroxy-2-undecyl-1,7-dioxadispiro[5.1.5.2]pentadeca-9,12-dien-11-one (Aculeatin F)C28H38O4[α]D25=-3.9 (c 0.6, CHCl3)Source of chirality: hydrolytic kinetic resolution and l-proline catalyze α-aminoxylationAbsolute configuration: (2R,4R,6R)
(2R,4R,6S)-4-Hydroxy-2-undecyl-1,7-dioxadispiro[5.1.5.2]pentadeca-9,12-dien-11-one (Aculeatin epi-F)C13H16O[α]D25=+44.2 (c 0.6, CHCl3)Source of chirality: hydrolytic kinetic resolution and l-proline catalyze α-aminoxylationAbsolute configuration: (2R,4R,6S)
(S)-Pentadec-1-en-4-yl acrylateC18H32O2[α]D25=+14.2 (c 0.7, CHCl3)Source of chirality: hydrolytic kinetic resolution and l-proline catalyze α-aminoxylationAbsolute configuration: (4S)
(S)-6-Undecyl-5,6-dihydro-2H-pyran-2-oneC16H28O2[α]D25=-78.2 (c 0.9, THF)Source of chirality: hydrolytic kinetic resolution and l-proline catalyze α-aminoxylationAbsolute configuration: (6S)
(S)-6-Undecyltetrahydro-2H-pyran-2-oneC16H30O2[α]D25=-42.2 (c 1.2, THF)Source of chirality: hydrolytic kinetic resolution and l-proline catalyze α-aminoxylationAbsolute configuration: (6S)
(R)-6-Undecyltetrahydro-2H-pyran-2-oneC16H30O2[α]D25=+41.8 (c 1.5, THF)Source of chirality: hydrolytic kinetic resolution and l-proline catalyze α-aminoxylationAbsolute configuration: (6R)
(S)-tert-Butyl pentadec-1-en-4-ylcarbamateC20H39NO2[α]D25=-2.9 (c 1.6, CHCl3)Source of chirality: hydrolytic kinetic resolution and l-proline catalyze α-aminoxylationAbsolute configuration: (4S)
(S)-tert-Butyl allyl(pentadec-1-en-4-yl)carbamateC23H43NO2[α]D25=-5.0 (c 1.0, CHCl3)Source of chirality: hydrolytic kinetic resolution and l-proline catalyze α-aminoxylationAbsolute configuration: (4S)
(S)-tert-Butyl 6-undecyl-5,6-dihydropyridine-1(2H)-carboxylateC21H39NO2[α]D25=-0.65 (c 1.5, CHCl3)Source of chirality: hydrolytic kinetic resolution and l-proline catalyze α-aminoxylationAbsolute configuration: (6S)
(S)-tert-Butyl 2-undecylpiperidine-1-carboxylateC21H41NO2[α]D25=-25.6 (c 0.6, CHCl3)Source of chirality: hydrolytic kinetic resolution and l-proline catalyze α-aminoxylationAbsolute configuration: (6S)
