메뉴 건너뛰기




Volumn 3, Issue 10, 2001, Pages 1535-1538

Enantioselective Strategy to the Spirocyclic Core of Palau'amine and Related Bisguanidine Marine Alkaloids

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMINE; BATZELLADINE A; GUANIDINE DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; SPIRO COMPOUND;

EID: 0035902247     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015864j     Document Type: Article
Times cited : (84)

References (32)
  • 8
    • 0043208390 scopus 로고    scopus 로고
    • note
    • The absolute configuration of these natural products has not been determined unambiguously; however, the absolute stereochemistry of palau'amine (as shown in Figure 1) has been tenatively assigned on the basis of similarities of its CD spectrum with monobromophakellin hydrochoride (see ref 2a).
  • 9
    • 0043208391 scopus 로고    scopus 로고
    • note
    • 50 of 42.8 nM in the mixed lymphocyte reaction (ref 2a).
  • 12
    • 0042206092 scopus 로고    scopus 로고
    • note
    • (a) This biosynthetic proposal was suggested by a reviewer of the publication by Kinnel and Scheuer (see footnote 23, ref 2b).
  • 13
    • 0035136516 scopus 로고    scopus 로고
    • (b) For a recently described unifying biosynthetic proposal of oroidin-derived metabolites, see: Mourabit, A. A.; Potier, P. Eur. J. Org. Chem. 2001, 237-243.
    • (2001) Eur. J. Org. Chem. , pp. 237-243
    • Mourabit, A.A.1    Potier, P.2
  • 14
  • 17
    • 0019965054 scopus 로고
    • Dienophile 9 was synthesized from (S)-pyroglutamic acid (five steps) in analogy to reported procedures for related dienophiles; see: (a) Ohfune, Y.; Tomita, M. J. Am. Chem. Soc. 1982, 104, 3511-3513.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 3511-3513
    • Ohfune, Y.1    Tomita, M.2
  • 19
    • 0042206091 scopus 로고    scopus 로고
    • note
    • Current efforts are directed toward the presumed enantiomeric tricyclic core structure in order to utilize the less expensive (S)-pyroglutamic acid.
  • 26
    • 0043208384 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details.
  • 28
    • 0034658874 scopus 로고    scopus 로고
    • We thank Dr. Eric Moher (Eli Lilly) for bringing this related work to our attention
    • For a Baeyer-Villiger oxidation of an oxocarbenium ion, see: Hunt, K. W.; Grieco, P. A. Org. Lett. 2000, 2, 1717-1719. We thank Dr. Eric Moher (Eli Lilly) for bringing this related work to our attention.
    • (2000) Org. Lett. , vol.2 , pp. 1717-1719
    • Hunt, K.W.1    Grieco, P.A.2
  • 31
    • 0041705604 scopus 로고    scopus 로고
    • note
    • GOESY experiments shown were performed on spirocycle 20 and a deprotected derivative. See Supporting Information for details.
  • 32
    • 0043208388 scopus 로고    scopus 로고
    • note
    • Substantial quantities of aromatized byproducts were produced unless cyclohexene was added as an "alkene buffer". An example of this concept (unpublished results of J. J. Hans) was described to us recently by Professor T. R. Hoye.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.