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Volumn 48, Issue 14, 2009, Pages 2580-2583

Total synthesis of (-)-FR182877 through tandem IMDA-IMHDA reactions and stereoselective transition-metal-mediated transformations

Author keywords

Antitumor Agents; Cycloaddition; Natural products; Polycycles; Strained molecules

Indexed keywords

ANTITUMOR AGENTS; CYTOTOXIC; DIELS-ALDER REACTION; EPIMERIZATION; INTELLIGENT DESIGNS; NATURAL PRODUCTS; POLYCYCLES; STEREO-SELECTIVE; STEREOSELECTIVE REDUCTION; STRAINED MOLECULES; TOTAL SYNTHESIS; TRANSITION-METAL-MEDIATED;

EID: 70349878406     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200900097     Document Type: Article
Times cited : (33)

References (47)
  • 1
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    • 50 values of (-)-FR182877 are 0.05-0.18 nm depending on the cell line; a) B. Sato, H. Muramatsu, M. Miyauchi, Y. Hori, S. Takese, M. Hino, S. Hashimoto, H. Terano, J. Antibiot. 2000, 53, 123-130;
    • 50 values of (-)-FR182877 are 0.05-0.18 nm depending on the cell line; a) B. Sato, H. Muramatsu, M. Miyauchi, Y. Hori, S. Takese, M. Hino, S. Hashimoto, H. Terano, J. Antibiot. 2000, 53, 123-130;
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    • see the Supporting Information
    • c) R. M. Buey et al., see the Supporting Information, Nat. Chem. Biol. 2007, 3, 117-125;
    • (2007) Nat. Chem. Biol , vol.3 , pp. 117-125
    • Buey, R.M.1
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    • For the preparation of compound 1, see the Supporting Information.
    • For the preparation of compound 1, see the Supporting Information.
  • 23
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    • [4d] in all respects.
    • [4d] in all respects.
  • 24
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    • A similar trend in stereoselectivity has been reported for the IMDA reaction producing trans-dehydrodecaline derivatives. For recent examples, see: G. N. Varseev, M. E. Maier, Angew. Chem. 2006, 118, 4885-4889;
    • A similar trend in stereoselectivity has been reported for the IMDA reaction producing trans-dehydrodecaline derivatives. For recent examples, see: G. N. Varseev, M. E. Maier, Angew. Chem. 2006, 118, 4885-4889;
  • 25
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    • and references therein
    • Angew. Chem. Int. Ed. 2006, 45, 4767-4771, and references therein.
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 4767-4771
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    • 30744456747 scopus 로고    scopus 로고
    • and references therein. Reviews on the IMDA reaction
    • Reviews on the IMDA reaction: K. Takao, R. Munakata, K. Tadano, Chem. Rev. 2005, 105, 4779-4807, and references therein.
    • (2005) Chem. Rev , vol.105 , pp. 4779-4807
    • Takao, K.1    Munakata, R.2    Tadano, K.3
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    • 4 gave no products.
    • 4 gave no products.
  • 28
    • 70349974942 scopus 로고    scopus 로고
    • Extensive studies on the cyclization through the ruthenium-mediated C-H activation provided no products
    • Extensive studies on the cyclization through the ruthenium-mediated C-H activation provided no products.
  • 29
    • 7044235861 scopus 로고    scopus 로고
    • Review on the intramolecular Heck reaction: a E. Negishi, C. Coperet, S. Ma, S. Y. Liou, F. Liu, Chem. Rev. 1996, 96, 365-394.
    • Review on the intramolecular Heck reaction: a) E. Negishi, C. Coperet, S. Ma, S. Y. Liou, F. Liu, Chem. Rev. 1996, 96, 365-394.
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    • Successful applications of the palladium-mediated 7-exo-trig cyclization to natural product synthesis: b J. Jin, S. M. Weinreb, J. Am. Chem. Soc. 1997, 119, 2050-2051;
    • Successful applications of the palladium-mediated 7-exo-trig cyclization to natural product synthesis: b) J. Jin, S. M. Weinreb, J. Am. Chem. Soc. 1997, 119, 2050-2051;
  • 33
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    • Other examples: e B. M. Trost, J. M. D. Fortunak, Organo-metallics 1982, 1, 7-13;
    • Other examples: e) B. M. Trost, J. M. D. Fortunak, Organo-metallics 1982, 1, 7-13;
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    • 70349973219 scopus 로고    scopus 로고
    • A mixture of compounds 8a and 8b was used for the reactions because separately the two compounds yielded almost the same results.
    • A mixture of compounds 8a and 8b was used for the reactions because separately the two compounds yielded almost the same results.
  • 46
    • 70349976481 scopus 로고    scopus 로고
    • -1) than its C18 epimer.
    • -1) than its C18 epimer.
  • 47
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    • All other new reagents, reported after the total synthesis by Evans, did not improve the yield
    • T. Mukaiyama, M. Usui, K. Saigo, Chem. Lett. 1976, 49-50. All other new reagents, reported after the total synthesis by Evans, did not improve the yield.
    • (1976) Chem. Lett , pp. 49-50
    • Mukaiyama, T.1    Usui, M.2    Saigo, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.