Title:
SUBSTITUTED OPEN-CHAIN TERPENE COMPOUND
Document Type and Number:
WIPO Patent Application WO/1991/008186
Kind Code:
A1
Abstract:
A novel substituted open-chain terpene compound of general formula (I) which is useful as an intermediate for the synthesis of sarcophytol A, wherein R is ($g(a)), ($g(b)), or ($g(c)) (wherein R?1¿ is cyano or formyl R?2¿ is hydrogen or CO¿2?R?3¿, R?3¿ is C¿1? to C¿4? alkyl, and R?4¿ is -C=CH or -CH=CH¿2?); X is hydrogen, hydroxyl, halogen, OR?5¿ or OSO¿2?R?6¿ (wherein R?5¿ is hydrogen, 1-alkoxyalkyl, tetrahydrofuryl, tetrahydropyranyl, acyl, or silyl substituted by C¿1? to C¿5? alkyl or phenyl, and R?6¿ is C¿1? to C¿4? alkyl which may be substituted by halogen or phenyl which may be substituted by C¿1? to C¿4? alkyl); and n is an integer of 0 to 2, provided that X is OR?5¿ and n is O when R is ($g(b)) or ($g(c)); X is neither halogen nor OSO¿2?R?6¿ when R?1¿ is formyl; R?2¿ is not hydrogen when R?5¿ is hydrogen; and R?3¿ is not methyl when R?5¿ is 1-ethoxyethyl.
Inventors:
TAKAYANAGI HISAO (JP)
KITANO YASUNORI (JP)
MORINAKA YASUHIRO (JP)
KITANO YASUNORI (JP)
MORINAKA YASUHIRO (JP)
Application Number:
PCT/JP1990/001555
Publication Date:
June 13, 1991
Filing Date:
November 29, 1990
Export Citation:
Assignee:
MITSUBISHI CHEM IND (JP)
International Classes:
C07C33/02; C07C43/178; C07C43/315; C07C45/44; C07C45/51; C07C45/63; C07C45/67; C07C47/21; C07C47/24; C07C47/263; C07C47/277; C07C49/203; C07C49/227; C07C49/24; C07C49/255; C07C49/587; C07C69/007; C07C69/738; C07C255/07; C07C255/10; C07C255/15; C07C255/46; C07C309/65; C07D309/06; C07D309/12; C07F7/18; (IPC1-7): C07C33/02; C07C33/048; C07C43/14; C07C43/15; C07C43/188; C07C47/21; C07C47/263; C07C49/255; C07C69/738; C07C69/78; C07C255/07; C07C255/15; C07C309/66; C07C309/73; C07F7/18
Foreign References:
| US4510319A | 1985-04-09 | |||
| JPS5214711A | 1977-02-03 |
Other References:
Biocatalysis, Vol. 2, No. 1, (1988), H. A. ARFMANN et al. "Microbial. omega. - hydroxylation of trans - nerolidol and structurally related sesquiterpenoids", p. 59-67.
Yakugaku Zasshi, Vol. 106, No. 1, (1986), HIROSHI WADA "Chemistry and Chemotaxonomy of Ferns (report No. 66); Chemical study of gradients of Ibuki-fern and Oibuki-fern", p. 989-994.
Tetrahedron Letters, Vol. 25, No. 38, (1984), J. E. McMURRY et al. "A method for the palladiumcatalyzed allylic oxidation of olefins", p. 4187-4190.
Tetrahedron Letters, Vol. 24, No. 33, (1983), T. TAKAHASHI et al. "A first total synthesis of germacrone by intramolecular alkylation of protected cyanohydrin", p. 3489-3492.
Phytochemistry, Vol. 21, No. 10, (1982), F. BOHLMANN et al. "Natural occurring terpene derivatives. Part 457. Three furanoheliangolides from calea villosa", p. 2593-2595.
Phytochemistry, Vol. 21, No. 6, (1982), F. BOHLMANN et al. "Naturally occurring terpene derivatives. Part 395. Guainolides and furanosesquiterpenes from Ursinianana", p. 1309-1312.
Phytochemistry, Vol. 21, No. 5, (1982), F. BOHLMANN et al. "Naturally occurring terpene derivatives. Part 414. New guaianolides from Pseudostifftia Kingii", p. 1171-1172.
Phytochemistry, Vol. 21, No. 3, (1982), F. BOHLMANN et al. "Naturally occurring terpene derivatives. Part 377. An epoxygermacranolide and further constituents from Mikania species", p. 705-707.
Phytochemistry, Vol. 20, No. 4, (1981), F. BOHLMANN et al. "Naturally occurring terpene derivatives. Part 301. Fourteen heliangolides from Calea species", p. 743-749.
Phytochemistry, Vol. 19, No. 4, (1980), F. BOHLMANN et al. "Naturally occurring terpene derivatives. Part 243. New sesquiterpene lactones and nerolidol derivatives from Ursinia species", p. 587-591.
Tetrahedron Letters, Vol. 31, No. 23, (1990), H. TAKAYANAGI et al. "Stereo- and enantioselective total synthesis of sarcophytol-A", p. 3317-3320.
See also references of EP 0455826A4
Yakugaku Zasshi, Vol. 106, No. 1, (1986), HIROSHI WADA "Chemistry and Chemotaxonomy of Ferns (report No. 66); Chemical study of gradients of Ibuki-fern and Oibuki-fern", p. 989-994.
Tetrahedron Letters, Vol. 25, No. 38, (1984), J. E. McMURRY et al. "A method for the palladiumcatalyzed allylic oxidation of olefins", p. 4187-4190.
Tetrahedron Letters, Vol. 24, No. 33, (1983), T. TAKAHASHI et al. "A first total synthesis of germacrone by intramolecular alkylation of protected cyanohydrin", p. 3489-3492.
Phytochemistry, Vol. 21, No. 10, (1982), F. BOHLMANN et al. "Natural occurring terpene derivatives. Part 457. Three furanoheliangolides from calea villosa", p. 2593-2595.
Phytochemistry, Vol. 21, No. 6, (1982), F. BOHLMANN et al. "Naturally occurring terpene derivatives. Part 395. Guainolides and furanosesquiterpenes from Ursinianana", p. 1309-1312.
Phytochemistry, Vol. 21, No. 5, (1982), F. BOHLMANN et al. "Naturally occurring terpene derivatives. Part 414. New guaianolides from Pseudostifftia Kingii", p. 1171-1172.
Phytochemistry, Vol. 21, No. 3, (1982), F. BOHLMANN et al. "Naturally occurring terpene derivatives. Part 377. An epoxygermacranolide and further constituents from Mikania species", p. 705-707.
Phytochemistry, Vol. 20, No. 4, (1981), F. BOHLMANN et al. "Naturally occurring terpene derivatives. Part 301. Fourteen heliangolides from Calea species", p. 743-749.
Phytochemistry, Vol. 19, No. 4, (1980), F. BOHLMANN et al. "Naturally occurring terpene derivatives. Part 243. New sesquiterpene lactones and nerolidol derivatives from Ursinia species", p. 587-591.
Tetrahedron Letters, Vol. 31, No. 23, (1990), H. TAKAYANAGI et al. "Stereo- and enantioselective total synthesis of sarcophytol-A", p. 3317-3320.
See also references of EP 0455826A4
Attorney, Agent or Firm:
Aoyama, Tamotsu (IMP Building 3-7, Shiromi 1-chome, Chuo-k, Osaka-shi Osaka 540, JP)
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