Title:
CIS-3,5-DISUBSTITUTED-DIHYDRO-FURAN-2-ONES AND THE PREPARATION AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO2005014565
Kind Code:
A3
Abstract:
The present invention relates to an improved process to prepare cis-3-dihydrocarbylmethano-5-hydrocarbyldihydro-furan-2-ones. The present invention also relates to novel compositions of matter comprising enantiomerically pure cis-3-dihydrocarbylmethano-5-hydrocarbyldihydro-furan-2-ones, being the (3S,5S), (3R,5R), (3S,5R), or (3R,5S) optically pure isomers, and a new, more cost efficient process to prepare said optically pure isomers.
Inventors:
FAGAN PAUL JOSEPH (US)
BRANDENBURG CHARLES J (US)
BRANDENBURG CHARLES J (US)
Application Number:
PCT/US2004/025668
Publication Date:
April 07, 2005
Filing Date:
August 06, 2004
Export Citation:
Assignee:
DU PONT (US)
FAGAN PAUL JOSEPH (US)
BRANDENBURG CHARLES J (US)
FAGAN PAUL JOSEPH (US)
BRANDENBURG CHARLES J (US)
International Classes:
C07D307/33; C07D315/00; C11B9/00; (IPC1-7): C07D315/00; C07D307/32; C11B9/00
Foreign References:
| US20020143195A1 | 2002-10-03 | |||
| US4980342A | 1990-12-25 |
Other References:
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URABE H ET AL: "Reagent-controlled Stereoselection in Radical Addition to alpha-Methylenebutyrolactones", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, CHEMICAL SOCIETY. LETCHWORTH, GB, 1995, pages 1043 - 1044, XP009043357, ISSN: 0022-4936
SUNG H K ET AL: "An asymmetric synthesis of a key intermediate to 1beta-methylcarbapenem antibiotics", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 36, no. 37, 11 September 1995 (1995-09-11), pages 6713 - 6716, XP004027323, ISSN: 0040-4039
BARRETT A G M ET AL: "Total synthesis of (+)-milbemycin beta3", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 51, no. 25, 12 December 1986 (1986-12-12), pages 4840 - 4856, XP002273308, ISSN: 0022-3263
CLARK STILL W ET AL: "Remote Asymmetric Induction. A Stereoselective Approach to Acyclic Diols via Cyclic Hydroboration", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 102, 1980, pages 7385 - 7387, XP002182870, ISSN: 0002-7863
DATABASE CROSSFIRE BEILSTEIN BEILSTEIN INSTITUT ZUR FOERDERUNG DER WISSENSCHAFTEN, FRANKFURT AM MAIN, DE; 1988, XP002316016
GIERASCH T M ET AL: "Extensively Stereodiversified Scaffolds for use in Diversity-Oriented Library Synthesis", ORGANIC LETTERS, ACS, WASHINGTON, DC, US, vol. 5, no. 5, 2 May 2003 (2003-05-02), pages 621 - 624, XP002316011, ISSN: 1523-7060
REISSIG H U ET AL: "Ester Groups as Effective Ligands in Chelate-Controlled Additions of Cuprates and Grignard Reagents to Chiral beta-Formyl Esters", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 58, 1993, pages 6280 - 6285, XP002316012, ISSN: 0022-3263
KEMPF D J: "Dipeptide Analogues: Versatile Synthesis of the Hydroxyethyene Isostere", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 51, no. 21, 1986, pages 3921 - 3926, XP002316013, ISSN: 0022-3263
MCWILLIAMS J C ET AL: "Tandem Asymmetric Transformations", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 118, 1996, pages 11970 - 11971, XP002316014, ISSN: 0002-7863
NAKAMURA E ET AL: "Trichlorotitanium and Alkoxytitanium Homoenolates. Preparation, Characterization, and Utilization for Organic Synthesis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 108, 1986, pages 3745 - 3755, XP002316015, ISSN: 0002-7863
URABE H ET AL: "Reagent-controlled Stereoselection in Radical Addition to alpha-Methylenebutyrolactones", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, CHEMICAL SOCIETY. LETCHWORTH, GB, 1995, pages 1043 - 1044, XP009043357, ISSN: 0022-4936
SUNG H K ET AL: "An asymmetric synthesis of a key intermediate to 1beta-methylcarbapenem antibiotics", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 36, no. 37, 11 September 1995 (1995-09-11), pages 6713 - 6716, XP004027323, ISSN: 0040-4039
BARRETT A G M ET AL: "Total synthesis of (+)-milbemycin beta3", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 51, no. 25, 12 December 1986 (1986-12-12), pages 4840 - 4856, XP002273308, ISSN: 0022-3263
CLARK STILL W ET AL: "Remote Asymmetric Induction. A Stereoselective Approach to Acyclic Diols via Cyclic Hydroboration", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 102, 1980, pages 7385 - 7387, XP002182870, ISSN: 0002-7863
DATABASE CROSSFIRE BEILSTEIN BEILSTEIN INSTITUT ZUR FOERDERUNG DER WISSENSCHAFTEN, FRANKFURT AM MAIN, DE; 1988, XP002316016
GIERASCH T M ET AL: "Extensively Stereodiversified Scaffolds for use in Diversity-Oriented Library Synthesis", ORGANIC LETTERS, ACS, WASHINGTON, DC, US, vol. 5, no. 5, 2 May 2003 (2003-05-02), pages 621 - 624, XP002316011, ISSN: 1523-7060
REISSIG H U ET AL: "Ester Groups as Effective Ligands in Chelate-Controlled Additions of Cuprates and Grignard Reagents to Chiral beta-Formyl Esters", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 58, 1993, pages 6280 - 6285, XP002316012, ISSN: 0022-3263
KEMPF D J: "Dipeptide Analogues: Versatile Synthesis of the Hydroxyethyene Isostere", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 51, no. 21, 1986, pages 3921 - 3926, XP002316013, ISSN: 0022-3263
MCWILLIAMS J C ET AL: "Tandem Asymmetric Transformations", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 118, 1996, pages 11970 - 11971, XP002316014, ISSN: 0002-7863
NAKAMURA E ET AL: "Trichlorotitanium and Alkoxytitanium Homoenolates. Preparation, Characterization, and Utilization for Organic Synthesis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 108, 1986, pages 3745 - 3755, XP002316015, ISSN: 0002-7863
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