Title:
METHOD FOR SYNTHESIS OF CIGUATOXIN CTX1B AND COMPOUND USEFUL FOR THE SYNTHESIS OF CIGUATOXIN CTX1B
Document Type and Number:
WIPO Patent Application WO/2007/083638
Kind Code:
A1
Abstract:
Disclosed is a method for total synthesis of CTX1B, which is developed for the synthesis of a ciguatoxin analogue such as CTX3C and enables the more efficient application of an established reaction to the total synthesis of CTX1B. More specifically, disclosed is a method for total synthesis of CTX1B comprising: an O,S-acetal formation reaction for synthesizing a novel compound (3); a radical cyclization reaction for constructing a 9-membered ring formation reaction including a novel compound (6) through a novel compound (8) and yielding a compound (D); and a deprotection reaction for yielding CTX1B. Also disclosed are novel compounds (1) to (8) which are particularly useful for the synthesis of CTX1B and can be used for the synthesis of a ciguatoxin analogue.
Inventors:
HIRAMA MASAHIRO (JP)
INOUE MASAYUKI (JP)
INOUE MASAYUKI (JP)
Application Number:
PCT/JP2007/050545
Publication Date:
July 26, 2007
Filing Date:
January 10, 2007
Export Citation:
Assignee:
JAPAN SCIENCE & TECH AGENCY (JP)
HIRAMA MASAHIRO (JP)
INOUE MASAYUKI (JP)
HIRAMA MASAHIRO (JP)
INOUE MASAYUKI (JP)
International Classes:
C07D493/22; C07D519/00; C07F7/18; C07B61/00
Other References:
TATAMI A. ET AL.: "A concise route to the right wing of ciguatoxin", TETRAHEDRON LETTERS, vol. 44, no. 28, 2003, pages 5229 - 5233, XP004430953
KOBAYASHI S. ET AL.: "Synthesis of the fully functionalized ABCDE ring moiety of ciguatoxin", ORG. LETT., vol. 6, no. 5, 2004, pages 751 - 754, XP003015463
INOUE M. ET AL.: "First- and second-generation total synthesis of ciguatoxin CTX3C", PROC. NATL. ACAD. SCI. USA, vol. 101, no. 33, 2004, pages 12013 - 12018, XP003015464
INOUE M. ET AL.: "Total synthesis of ciguatoxin and 51-hydroxy CTX3C", J. AM. CHEM. SOC., vol. 128, no. 29, 2006, pages 9352 - 9354, XP003015465
KOBAYASHI S. ET AL.: "Synthesis of the fully functionalized ABCDE ring moiety of ciguatoxin", ORG. LETT., vol. 6, no. 5, 2004, pages 751 - 754, XP003015463
INOUE M. ET AL.: "First- and second-generation total synthesis of ciguatoxin CTX3C", PROC. NATL. ACAD. SCI. USA, vol. 101, no. 33, 2004, pages 12013 - 12018, XP003015464
INOUE M. ET AL.: "Total synthesis of ciguatoxin and 51-hydroxy CTX3C", J. AM. CHEM. SOC., vol. 128, no. 29, 2006, pages 9352 - 9354, XP003015465
Attorney, Agent or Firm:
MIYAMOTO, Harumi (19-14 Toranomon 1-chome, Minato-k, Tokyo ., JP)
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