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Volumn 45, Issue 26, 2006, Pages 4345-4348

Regiocontrol in MnIII-mediated oxidative heterobicyclizations: access to the core skeletons of oroidin dimers

Author keywords

Cascade reactions; Natural products; Radical reactions; Rearrangement; Synthetic methods

Indexed keywords

CASCADE REACTIONS; NATURAL PRODUCTS; REARRANGEMENTS; SYNTHETIC METHODS;

EID: 33746288746     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601208     Document Type: Article
Times cited : (69)

References (31)
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    • and references therein
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    • For a review of radical cascade cyclizations, see: a) A. J. McCarroll, J. C. Walton, Angew. Chem. 2001, 113, 2282-2307;
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    • For reviews, see: a) G. G. Melikyan, Org. React. 1997, 49, 427-675;
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    • III-promoted cyclization of allylic β-dicarboxylate is more common, for example, Ref. [5].
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    • Sung, K.1    Wang, Y.Y.2
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    • For a two-step oxidation of imidazolinone with dimethyldioxirane (DMDO)/N-chlorosuccinimide (NCS) to construct the palau'amine core skeleton, see: a) A. S. Dilley, D. Romo, Org. Lett. 2001, 3, 1535-1538;
    • (2001) Org. Lett. , vol.3 , pp. 1535-1538
    • Dilley, A.S.1    Romo, D.2
  • 27
    • 33746273963 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of the crude product indicated a clean transformation; however, the cyclization products were not stable to column chromatography on silica gel (among all the isolation conditions examined, Davisil 633 silica gel provided the best yields of the isolated products).
  • 28
    • 33645897192 scopus 로고
    • 1,3 strain, see: R. W. Hoffmann, Chem. Rev. 1989, 89, 1841-1860.
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  • 29
    • 33746307753 scopus 로고    scopus 로고
    • For a similar stereospecificity issue, see: Ref. [6]
    • For a similar stereospecificity issue, see: Ref. [6].
  • 30
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    • note
    • A slightly higher temperature (80°C) was required to suppress the formation of the monocyclization product; however, the diastereoselectivity was compromised.
  • 31
    • 33746315864 scopus 로고    scopus 로고
    • CCDC-290044 (15) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.