Title:
アミノステロール、ビタミンD類似体および他の化合物の製造に有用な24-ヒドロキシル化された化合物の立体選択的合成
Document Type and Number:
Japanese Patent JP4441769
Kind Code:
B2
Abstract:
A method is described for stereoselectively reducing an unsaturated alkyl ketone substituent attached to a fused ring base. In this method, the unsaturated alkyl ketone reacts with a chiral oxazaborolidine reagent. This reaction stereoselectively reduces the unsaturated alkyl ketone to an unsaturated alkyl alcohol. The unsaturated alkyl alcohol can be further reduced, if desired, to produce a saturated alkyl alcohol. The fused ring base can be, for example, a steroid ring base or a base of a vitamin D analog. The process in accordance with the invention can be used with an alkeneone substituent (e.g., a 22-ene-24-one substituent) or an alkyneone substituent (e.g., a 22-yne-24-one substituent) on a steroid ring base to make squalamine or other useful aminosterol compounds and intermediates for making aminosterol compounds.
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Inventors:
Kinney, William, A.
Johns, Stephen
Tsang, Shwe Hai
Lao, Mina, N.
Briard, michel
Harold, Meckler
Lee, Nancy
Johns, Stephen
Tsang, Shwe Hai
Lao, Mina, N.
Briard, michel
Harold, Meckler
Lee, Nancy
Application Number:
JP52401298A
Publication Date:
March 31, 2010
Filing Date:
December 08, 1997
Export Citation:
Assignee:
Genera Corporation
International Classes:
C07J9/00; C07J31/00; C07J41/00
Domestic Patent References:
| JP6329679A | ||||
| JP11506775A | ||||
| JP2002515019A |
Foreign References:
| US4943635 | ||||
| WO1994019366A1 |
Other References:
S. WALLBAUM ET AL, Asymmetric Syntheses with Chiral Oxazaborolidines, TETRAHEDRON: ASYMMETRY, 1992年, vol. 3, no. 12, pages 1475-1504
COREY E J ET AL, A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES. APPLICATIONS TO MULTISTEP SYNTHESES, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987年, vol. 109, no. 25, page 7925-7926
M. ISHIGURO ET AL, Neighbouring Group Effects. Part 2. Effect of Epoxide on the Hydrolysis of Adjacent Acetate Groups, JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, 1980年, no. 11, pages 2507-2510
PARKER K A ET AL, Asymmetric Reduction. A Convenient Method for the Reduction of Alkynyl Ketones, J. ORG. CHEM., 1996年, VOL.61 (9), PP.3214-3217
J. Org. Chem., 1995年, Volume 60, Issue 16, pp 5121-5126
COREY E J ET AL, A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES. APPLICATIONS TO MULTISTEP SYNTHESES, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987年, vol. 109, no. 25, page 7925-7926
M. ISHIGURO ET AL, Neighbouring Group Effects. Part 2. Effect of Epoxide on the Hydrolysis of Adjacent Acetate Groups, JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, 1980年, no. 11, pages 2507-2510
PARKER K A ET AL, Asymmetric Reduction. A Convenient Method for the Reduction of Alkynyl Ketones, J. ORG. CHEM., 1996年, VOL.61 (9), PP.3214-3217
J. Org. Chem., 1995年, Volume 60, Issue 16, pp 5121-5126
Attorney, Agent or Firm:
Hidesaku Yamamoto