Title:
新規化合物、その製造方法及び中間体
Document Type and Number:
Japanese Patent JP4135258
Kind Code:
B2
Abstract:
PROBLEM TO BE SOLVED: To obtain Neplanocin A having strong carcinostatic action in a good yield by the short production process of reverse Diels-Alder reactions of an intermediate obtained from cyclopentadiene and 1,4-benzoquinone. SOLUTION: Neplanocin A is obtained by reacting a compound of formula I (R and R are each H or a 2-20C alkanoyl) as a starting raw material with a halogenation agent, by protecting the hydroxyl group of the resultant product, by treating it with an oxidizing agent, by reacting the product with an acetalizing agent, by dehalogenation to obtain a compound of formula II (Y is a protecting group), by the reverse Diels-Alder reaction of the compound of formula II, by treating the resultant product with an oxidizing agent or the like, by O. Mitsunobu synthesis of the product and by deblocking. For example, the compound of formula I is new and is obtained by the transesterification of a racemate of formula III with an acylating agent in the presence of a hydrolase. Not only compound of formula II but also other intermediates in the above reaction are all new.
Inventors:
Naoyuki Yoshida
Kunio Ogasawara
Kunio Ogasawara
Application Number:
JP14315599A
Publication Date:
August 20, 2008
Filing Date:
May 24, 1999
Export Citation:
Assignee:
Chisso Co., Ltd.
International Classes:
C07C35/37; C12P41/00; C07C69/16; C07D307/77; C07D317/70; C07F7/12; C07F7/18; C07B57/00
Domestic Patent References:
| JP5170765A | ||||
| JP4021682A |
Other References:
Shiozaki, M. et. al.,Synthesis of 6-epi-trehazolin from D-ribonolactone: evidence for the non-existence of a 5,6-ring fused structural isomer of 6-epi-trehazolin,Tetrahedron Letters,1994年,35(6),887-890
Shiozaki, M. et al.,Stereocontrolled Syntheses of 6-epi-Trehazolin and 6-epi-Trehalamine from D-Ribonolactone,Journal of Organic Chemistry,1994年,59(16),4450-4460
Hill, J. M. et. al.,Revised pathway for the biosynthesis of aristeromycin and neplanocin A from D-glucose in Streptomyces citricolor,Journal of the American Chemical Society,1995年,117(19),5391-5392
Niizuma, S. et. al.,New neplanocin analog. 10. The conversion of adenosine to neplanocin A, a carbocyclic nucleoside antibiotic with potent antiviral activity,Tetrahedron,1997年,53(40),13621-13632
Ohira, S. et.al.,Synthesis of (-)-neplanocin A via C-H insertion of alkylidenecarbene,Tetrahedron Letters,1995年,36(9),1537-1538
Yoshida, N. et. al.,A concise synthesis of (-)-neplanocin A,Tetrahedron Letters,1998年,39(26),4677-4678
Shiozaki, M. et al.,Stereocontrolled Syntheses of 6-epi-Trehazolin and 6-epi-Trehalamine from D-Ribonolactone,Journal of Organic Chemistry,1994年,59(16),4450-4460
Hill, J. M. et. al.,Revised pathway for the biosynthesis of aristeromycin and neplanocin A from D-glucose in Streptomyces citricolor,Journal of the American Chemical Society,1995年,117(19),5391-5392
Niizuma, S. et. al.,New neplanocin analog. 10. The conversion of adenosine to neplanocin A, a carbocyclic nucleoside antibiotic with potent antiviral activity,Tetrahedron,1997年,53(40),13621-13632
Ohira, S. et.al.,Synthesis of (-)-neplanocin A via C-H insertion of alkylidenecarbene,Tetrahedron Letters,1995年,36(9),1537-1538
Yoshida, N. et. al.,A concise synthesis of (-)-neplanocin A,Tetrahedron Letters,1998年,39(26),4677-4678