Title:
PROCESS FOR PRODUCING HEXAHYDROFUROFURANOL DERIVATIVE, INTERMEDIATE THEREOF AND PROCESS FOR PRODUCING THE SAME
Document Type and Number:
WIPO Patent Application WO/2004/060895
Kind Code:
A1
Abstract:
A process for efficiently producing compound (XIV) being useful as a drug intermediate on an industrial scale at low cost without the need to use ozonization and highly toxic agents; and an intermediate for use in the process. In particular, a process for producing a compound having the absolute configuration of the formula (XV) or an enantiometric isomer thereof without the need to use means such as optical resolution; and an intermediate for use in the process. (1) Compound (XIV) is produced by deriving compound (I) from compound (XIII) as a starting material and sequentially performing introduction of a protective group, reduction and cyclization. Particularly, compound (XIV) is produced by deriving compound (I) through compound (XX) from compound (XIII) as a starting material. Compound having the absolute configuration of the formula (XV) or the like is produced in high stereoselectivity from optically active compound (XIII) as a starting material. (2) Compound (XXVI) is produced by deriving compound (XXII) from compound (XXI) as a starting material through stereoselective reduction thereof and sequentially performing introduction of a protective group, reduction and cyclization. Compound (XV) is produced by inverting hydroxyl of the compound (XXVI). (1) (2) wherein symbols are as defined in the description.
Inventors:
IKEMOTO TETSUYA (JP)
PIAO DONGGUO (JP)
PIAO DONGGUO (JP)
Application Number:
PCT/JP2003/013685
Publication Date:
July 22, 2004
Filing Date:
October 27, 2003
Export Citation:
Assignee:
SUMIKA FINE CHEMICALS CO LTD (JP)
IKEMOTO TETSUYA (JP)
PIAO DONGGUO (JP)
IKEMOTO TETSUYA (JP)
PIAO DONGGUO (JP)
International Classes:
C07C69/708; C07D307/20; C07D307/33; C07D407/04; C07D493/04; (IPC1-7): C07D493/04; C07D407/04; C07D307/32
Domestic Patent References:
| WO2003022853A1 | 2003-03-20 | |||
| WO2003024974A2 | 2003-03-27 | |||
| WO1999067417A2 | 1999-12-29 |
Foreign References:
| JPH04108782A | 1992-04-09 |
Other References:
EVANS DAVID A, ET AL: "C2-SYMMETRIC COPPER(II) COMPLEXES AS CHIRAL LEWIS ACIDS. CATALYTIC ENANTIOSELECTIVE ALDOL ADDITIONS OF SILYLKETENE ACETALS TO BENZYLOXYACETALDEHYDE", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 118, no. 24, 1996, pages 5814 - 5815, XP002089411
EVANS D A, ET AL: "C2-SYMMETRIC COPPER(II) COMPLEXES AS CHIRAL LEWIS ACIDS. SCOPE AND MECHANISM OF CATALYTIC ENANTIOSELECTIVE ALDOL ADDITIONS OF ENOLSILANES TO (BENZYLOXY)ACETALDEHYDE", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 121, no. 4, 1999, pages 669 - 685, XP001118229
TETRAHEDRON LETTERS, vol. 42, 2001, pages 4653
J. AM. CHEM. SOC., vol. 121, 1999, pages 669 - 685
See also references of EP 1589018A4
EVANS D A, ET AL: "C2-SYMMETRIC COPPER(II) COMPLEXES AS CHIRAL LEWIS ACIDS. SCOPE AND MECHANISM OF CATALYTIC ENANTIOSELECTIVE ALDOL ADDITIONS OF ENOLSILANES TO (BENZYLOXY)ACETALDEHYDE", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 121, no. 4, 1999, pages 669 - 685, XP001118229
TETRAHEDRON LETTERS, vol. 42, 2001, pages 4653
J. AM. CHEM. SOC., vol. 121, 1999, pages 669 - 685
See also references of EP 1589018A4
Attorney, Agent or Firm:
Takashima, Hajime (1-1 Fushimimachi 4-chome, Chuo-k, Osaka-shi Osaka, JP)
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