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Volumn 2, Issue 6, 2011, Pages 1086-1089

Benzoquinone-derived sulfinyl imines as versatile intermediates for alkaloid synthesis: Total synthesis of (-)-3-demethoxyerythratidinone

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONES; DIASTEREOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; ORGANOMETALLIC REAGENT; SYNTHETIC APPLICATION; TOTAL SYNTHESIS;

EID: 79957795447     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c1sc00095k     Document Type: Article
Times cited : (60)

References (43)
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    • (Ed: A. Brossi), Academic Press, Inc, San Diego
    • M. Matsui, in The Alkaloids, Chemistry and Pharmacology, Vol. 33 (Ed: A. Brossi), Academic Press, Inc, San Diego, 1988, pp 307-347.
    • (1988) The Alkaloids, Chemistry and Pharmacology , vol.33 , pp. 307-347
    • Matsui, M.1
  • 5
    • 0030924784 scopus 로고    scopus 로고
    • Reviews of nucleophilic 1,2-additions to imines
    • Reviews of nucleophilic 1,2-additions to imines: D. Enders and U. Reinhold, Tetrahedron: Asymmetry, 1997, 8, 1895-1946
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 1895-1946
    • Enders, D.1    Reinhold, U.2
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    • R. Bloch, Chem. Rev., 1998, 98, 1407-1438
    • (1998) Chem. Rev. , vol.98 , pp. 1407-1438
    • Bloch, R.1
  • 11
    • 33847713336 scopus 로고    scopus 로고
    • For a review of catalytic asymmetric additions to ketimines and ketones, see
    • For a review of catalytic asymmetric additions to ketimines and ketones, see: O. Riant and J. Hannedouche, Org. Biomol. Chem., 2007, 5, 873-888.
    • (2007) Org. Biomol. Chem. , vol.5 , pp. 873-888
    • Riant, O.1    Hannedouche, J.2
  • 12
    • 0033550526 scopus 로고    scopus 로고
    • Auxiliary based approaches
    • Auxiliary based approaches: J. A. Ellman and D. A. Cogan, J. Am. Chem. Soc., 1999, 121, 268-269
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 268-269
    • Ellman, J.A.1    Cogan, D.A.2
  • 24
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    • See Supporting Information
    • See Supporting Information.
  • 26
    • 79957863552 scopus 로고    scopus 로고
    • When n-BuLi is used, the debrominated product is observed in approximately 5% yield
    • When n-BuLi is used, the debrominated product is observed in approximately 5% yield.
  • 27
    • 79957792614 scopus 로고    scopus 로고
    • The relative stereochemistry of the major diastereomer of 8d was determined by X-ray diffraction and is consistent with addition through a six-membered chair-like transition state (see Ref. 9a). The relative stereochemistry of the remaining products was assigned in analogy based on spectroscopic analysis
    • The relative stereochemistry of the major diastereomer of 8d was determined by X-ray diffraction and is consistent with addition through a six-membered chair-like transition state (see Ref. 9a). The relative stereochemistry of the remaining products was assigned in analogy based on spectroscopic analysis.
  • 29
    • 79957835902 scopus 로고    scopus 로고
    • (-)-1 is the unnatural antipode. Both enantiomers of tertbutanesulfinamide are readily accessible; use of (S)-tertbutanesulfinamide should provide access to the natural antipode
    • (-)-1 is the unnatural antipode. Both enantiomers of tertbutanesulfinamide are readily accessible; use of (S)-tertbutanesulfinamide should provide access to the natural antipode.
  • 38
    • 0028213944 scopus 로고
    • All of the completed syntheses of enantioenriched 1 reported to date utilize chiral auxiliary strategies
    • All of the completed syntheses of enantioenriched 1 reported to date utilize chiral auxiliary strategies: Y. Tsuda, S. Hosoi, K. Ishida and M. Sangai, Chem. Pharm. Bull., 1994, 2, 204-213
    • (1994) Chem. Pharm. Bull. , vol.2 , pp. 204-213
    • Tsuda, Y.1    Hosoi, S.2    Ishida, K.3    Sangai, M.4
  • 42
    • 79957829266 scopus 로고    scopus 로고
    • Aryllithium 13 was previously utilized by Swenton andChou. SeeRef. 6a
    • Aryllithium 13 was previously utilized by Swenton andChou. SeeRef. 6a.
  • 43
    • 79957848095 scopus 로고    scopus 로고
    • Alternatively, cleavage of the tert-butanesulfinamide group can be effected under acidic conditions to deliver the free amine in excellent yield. See Supporting Information
    • Alternatively, cleavage of the tert-butanesulfinamide group can be effected under acidic conditions to deliver the free amine in excellent yield. See Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.