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Volumn 47, Issue 22, 2008, Pages 4200-4203

A general strategy for construction of both 2,6-cis- and 2,6-trans-disubstituted tetrahydropyrans: Substrate-controlled asymmetric total synthesis of (+)-scanlonenyne

Author keywords

Asymmetric synthesis; Bromination; Michael addition; Natural products; Tetrahydropyrans

Indexed keywords

CHEMICAL REACTIONS; KETONES; NETWORK PROTOCOLS; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 47049118956     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705663     Document Type: Article
Times cited : (30)

References (40)
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    • For reviews, see: a) T. L. B. Boivin, Tetrahedron 1987, 43, 3309-3362;
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  • 5
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    • For a lead reference concerning syntheses of 2,6-disubstituted tetrahydropyrans, see
    • a) For a lead reference concerning syntheses of 2,6-disubstituted tetrahydropyrans, see: N. Kawai, J.-M. Lagrange, M. Ohmi, J. Uenishi, J. Org. Chem. 2006, 71, 4530-4537;
    • (2006) J. Org. Chem , vol.71 , pp. 4530-4537
    • Kawai, N.1    Lagrange, J.-M.2    Ohmi, M.3    Uenishi, J.4
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    • Angew. Chem. Int. Ed. 2007, 46, 3326-3328.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 3326-3328
  • 8
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    • For an example of an intramolecular hetero-Michael addition to a hydroxybutenolide for construction of a pyrano-γ-lactone, see: G. A. Kraus, B. Roth, J. Org. Chem. 1978, 43, 4923-4924
    • For an example of an intramolecular hetero-Michael addition to a hydroxybutenolide for construction of a pyrano-γ-lactone, see: G. A. Kraus, B. Roth, J. Org. Chem. 1978, 43, 4923-4924.
  • 11
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    • and references therein;
    • Angew. Chem. Int. Ed. 2006, 45, 7199-7202, and references therein;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 7199-7202
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    • Angew. Chem. Int. Ed. 2007, 46, 4726-4728.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 4726-4728
  • 18
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    • For reviews of the Wacker oxidation, see: a
    • For reviews of the Wacker oxidation, see: a) J. Tsuji, Synthesis 1984, 369-384;
    • (1984) Synthesis , pp. 369-384
    • Tsuji, J.1
  • 20
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    • For the aldehyde-selective Wacker oxidation of allylic diol derivatives, see
    • For the aldehyde-selective Wacker oxidation of allylic diol derivatives, see: S.-K. Kang, K.-Y. Jung, J.-U. Chung, E.-Y. Namkoong, T.-H. Kim, J. Org. Chem. 1995, 60, 4678-4679.
    • (1995) J. Org. Chem , vol.60 , pp. 4678-4679
    • Kang, S.-K.1    Jung, K.-Y.2    Chung, J.-U.3    Namkoong, E.-Y.4    Kim, T.-H.5
  • 21
    • 53549088694 scopus 로고    scopus 로고
    • It is interesting to note that the Wacker oxidation of the C12/C13-anti isomer under comparable conditions gave the corresponding ketone as the major regioisomer; see the Supporting Information.
    • It is interesting to note that the Wacker oxidation of the C12/C13-anti isomer under comparable conditions gave the corresponding ketone as the major regioisomer; see the Supporting Information.
  • 23
    • 53549092596 scopus 로고    scopus 로고
    • CCDC-656345 (for 2), CCDC-667564 (for ent-3a), and CCDC-656346 (for 4b) contain 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; see also the Supporting Information.
    • CCDC-656345 (for 2), CCDC-667564 (for ent-3a), and CCDC-656346 (for 4b) contain 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; see also the Supporting Information.
  • 24
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    • -1, respectively.
    • -1, respectively.
  • 25
    • 53549112275 scopus 로고    scopus 로고
    • Separation of the 10R and 10S isomers and subjection of each isomer to the IHMA conditions gave roughly the same result. b The minor α,α′-cis isomer 3b did not equilibrate to the corresponding trans isomer 3a under the reaction conditions.
    • a) Separation of the 10R and 10S isomers and subjection of each isomer to the IHMA conditions gave roughly the same result. b) The minor α,α′-cis isomer 3b did not equilibrate to the corresponding trans isomer 3a under the reaction conditions.
  • 26
    • 53549123363 scopus 로고    scopus 로고
    • Independently synthesized 3′a equilibrated completely to 3′b after 80 h under the reaction conditions (≈ 30% after 24 h).
    • Independently synthesized 3′a equilibrated completely to 3′b after 80 h under the reaction conditions (≈ 30% after 24 h).
  • 33
    • 53549116000 scopus 로고    scopus 로고
    • 2 bromination of C13-ethyl, -vinyl, -(Z)-1-bromovinyl, -(E)-1-bromovinyl, and -1,1-dibromovinyl groups were 17, 13, 53, 10, and 77%, respectively.
    • 2 bromination of C13-ethyl, -vinyl, -(Z)-1-bromovinyl, -(E)-1-bromovinyl, and -1,1-dibromovinyl groups were 17, 13, 53, 10, and 77%, respectively.
  • 39
    • 53549089693 scopus 로고    scopus 로고
    • protection of the hydroxy group at the C10 position was critical for the success of the Weinreb ketone synthesis.
    • b) protection of the hydroxy group at the C10 position was critical for the success of the Weinreb ketone synthesis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.