Stereoselective synthesis of highly substituted bicyclic γ-lactones using homoaldol addition of 1-(1-cycloalkenyl)methyl carbamates

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Stereoselective synthesis of highly substituted bicyclic γ-lactones using homoaldol addition of 1-(1-cycloalkenyl)methyl carbamates. / Özlügedik, M.; Kristensen, Jesper Langgaard; Reuber, J.; Fröhlich, R.; Hoppe, D.

In: Synthesis, No. 14, 01.10.2004, p. 2303-2316.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Özlügedik, M, Kristensen, JL, Reuber, J, Fröhlich, R & Hoppe, D 2004, 'Stereoselective synthesis of highly substituted bicyclic γ-lactones using homoaldol addition of 1-(1-cycloalkenyl)methyl carbamates', Synthesis, no. 14, pp. 2303-2316. https://doi.org/10.1055/s-2004-831170

APA

Özlügedik, M., Kristensen, J. L., Reuber, J., Fröhlich, R., & Hoppe, D. (2004). Stereoselective synthesis of highly substituted bicyclic γ-lactones using homoaldol addition of 1-(1-cycloalkenyl)methyl carbamates. Synthesis, (14), 2303-2316. https://doi.org/10.1055/s-2004-831170

Vancouver

Özlügedik M, Kristensen JL, Reuber J, Fröhlich R, Hoppe D. Stereoselective synthesis of highly substituted bicyclic γ-lactones using homoaldol addition of 1-(1-cycloalkenyl)methyl carbamates. Synthesis. 2004 Oct 1;(14):2303-2316. https://doi.org/10.1055/s-2004-831170

Author

Özlügedik, M. ; Kristensen, Jesper Langgaard ; Reuber, J. ; Fröhlich, R. ; Hoppe, D. / Stereoselective synthesis of highly substituted bicyclic γ-lactones using homoaldol addition of 1-(1-cycloalkenyl)methyl carbamates. In: Synthesis. 2004 ; No. 14. pp. 2303-2316.

Bibtex

@article{88a64a6c49c84bbb921bc876e94c3f06,
title = "Stereoselective synthesis of highly substituted bicyclic γ-lactones using homoaldol addition of 1-(1-cycloalkenyl)methyl carbamates",
abstract = "Stereoselective addition of aldehydes 4 to metallated 1-(1-cycloalkenyl) methyl N,N-diisopropylcarbamates 1 gave cyclic homoaldol adducts 6. By applying the (-)-sparteine method, enantiomerically enriched products were obtained. These were oxidatively cyclized to diastereomerically pure ¿-lactones 8 via the ¿-lactol ethers 7. After deprotonation of ¿-lactones 8 with lithium hexamethyldisilazide, a further substitution was achieved. By trapping the lactone enolates 11 with {\ss}-naphthylmethyl bromide, single diastereomers of ¿-lactones 12 were produced.",
author = "M. {\"O}zl{\"u}gedik and Kristensen, {Jesper Langgaard} and J. Reuber and R. Fr{\"o}hlich and D. Hoppe",
year = "2004",
month = oct,
day = "1",
doi = "10.1055/s-2004-831170",
language = "English",
pages = "2303--2316",
journal = "Synthesis",
issn = "0039-7881",
publisher = "GeorgThieme Verlag",
number = "14",

}

RIS

TY - JOUR

T1 - Stereoselective synthesis of highly substituted bicyclic γ-lactones using homoaldol addition of 1-(1-cycloalkenyl)methyl carbamates

AU - Özlügedik, M.

AU - Kristensen, Jesper Langgaard

AU - Reuber, J.

AU - Fröhlich, R.

AU - Hoppe, D.

PY - 2004/10/1

Y1 - 2004/10/1

N2 - Stereoselective addition of aldehydes 4 to metallated 1-(1-cycloalkenyl) methyl N,N-diisopropylcarbamates 1 gave cyclic homoaldol adducts 6. By applying the (-)-sparteine method, enantiomerically enriched products were obtained. These were oxidatively cyclized to diastereomerically pure ¿-lactones 8 via the ¿-lactol ethers 7. After deprotonation of ¿-lactones 8 with lithium hexamethyldisilazide, a further substitution was achieved. By trapping the lactone enolates 11 with ß-naphthylmethyl bromide, single diastereomers of ¿-lactones 12 were produced.

AB - Stereoselective addition of aldehydes 4 to metallated 1-(1-cycloalkenyl) methyl N,N-diisopropylcarbamates 1 gave cyclic homoaldol adducts 6. By applying the (-)-sparteine method, enantiomerically enriched products were obtained. These were oxidatively cyclized to diastereomerically pure ¿-lactones 8 via the ¿-lactol ethers 7. After deprotonation of ¿-lactones 8 with lithium hexamethyldisilazide, a further substitution was achieved. By trapping the lactone enolates 11 with ß-naphthylmethyl bromide, single diastereomers of ¿-lactones 12 were produced.

UR - http://www.scopus.com/inward/record.url?scp=5644250666&partnerID=8YFLogxK

U2 - 10.1055/s-2004-831170

DO - 10.1055/s-2004-831170

M3 - Journal article

AN - SCOPUS:5644250666

SP - 2303

EP - 2316

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 14

ER -

ID: 45438453