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Volumn 7, Issue 20, 2005, Pages 4423-4426

Enantioselective total synthesis of tricyclic myrmicarin alkaloids

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; FUSED HETEROCYCLIC RINGS; MYRMICARIN;

EID: 26444462446     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051629f     Document Type: Article
Times cited : (41)

References (52)
  • 15
    • 84993918914 scopus 로고
    • Ester 13 is commercially available and can be prepared on > 30-g scale; see: Drinan, M. A.; Lash, T. D. J. Heterocycl. Chem. 1994, 31, 255-257.
    • (1994) J. Heterocycl. Chem. , vol.31 , pp. 255-257
    • Drinan, M.A.1    Lash, T.D.2
  • 24
    • 0027180141 scopus 로고
    • For reviews on the preparation and use of vinyl triflates, see: (a) Ritter, K. Synthesis 1993, 735-762.
    • (1993) Synthesis , pp. 735-762
    • Ritter, K.1
  • 27
    • 26444570992 scopus 로고    scopus 로고
    • XPhos is available from Strem Chemicals, Inc.
    • (b) XPhos is available from Strem Chemicals, Inc.
  • 36
    • 26444477071 scopus 로고    scopus 로고
    • note
    • The ee was determined by chiral HPLC analysis of a more advanced intermediate.
  • 37
    • 26444518869 scopus 로고    scopus 로고
    • note
    • Please see Supporting Information for details.
  • 38
    • 26444451764 scopus 로고    scopus 로고
    • note
    • 5
  • 39
    • 0004267670 scopus 로고
    • Wiley: New York
    • For reviews on the chemistry of pyrroles, see: (a) Pyrroles; Jones, A., Ed.; Wiley: New York, 1990,
    • (1990) Pyrroles
    • Jones, A.1
  • 42
    • 26444467805 scopus 로고    scopus 로고
    • note
    • Compounds not containing the C8-carbonyl in this series were found to be less stable toward storage as a result of decomposition and polymerization.
  • 49
    • 26444501131 scopus 로고    scopus 로고
    • note
    • The immediate air oxidation product of myrmicarins 215A, 215B, and 217 corresponds to myrmicarins 213A, 213B, and 215C, respectively.
  • 51
    • 26444455727 scopus 로고    scopus 로고
    • note
    • More forcing dehydration conditions and longer reaction times resulted in lower mass recovery and complications involving C6-C7 oxidation.
  • 52
    • 26444516177 scopus 로고    scopus 로고
    • note
    • Direct acidification of the reaction mixture can also provide myrmicarin 215B. See Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.