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Volumn 74, Issue 2, 2009, Pages 513-519

Asymmetric synthesis of the ABC-ring system of the antitumor antibiotic MPC1001

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; ACID-INDUCED CYCLIZATION; ANTITUMOR ANTIBIOTICS; ASYMMETRIC SYNTHESIS; DIKETOPIPERAZINE; ENOLATE; L PROLINES; NATURAL PRODUCTS; RING SYSTEMS; SULFUR ATOMS; TRICYCLIC COMPOUNDS;

EID: 60849111980     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802344t     Document Type: Article
Times cited : (32)

References (36)
  • 1
    • 4544259238 scopus 로고    scopus 로고
    • Isolation and structure of MPC1001: (a) Tsumagari, N.; Nakai, R.; Onodera, H.; Hasegawa, A.; Rahayu, E. S.; Ando, K.; Yamashita, Y. J. Antibiot. 2004, 57, 532-534.
    • Isolation and structure of MPC1001: (a) Tsumagari, N.; Nakai, R.; Onodera, H.; Hasegawa, A.; Rahayu, E. S.; Ando, K.; Yamashita, Y. J. Antibiot. 2004, 57, 532-534.
  • 8
    • 0016213528 scopus 로고
    • and references quoted therein
    • (b) Murdock, K. C. J. Med. Chem. 1974, 17, 827-835, and references quoted therein.
    • (1974) J. Med. Chem , vol.17 , pp. 827-835
    • Murdock, K.C.1
  • 13
    • 64549083614 scopus 로고    scopus 로고
    • For related compounds in which the disulfide bridge has been cleaved, see
    • For related compounds in which the disulfide bridge has been cleaved, see:
  • 19
    • 64549134166 scopus 로고    scopus 로고
    • Chemokine receptor antagonist activity, ref 1c; antiviral activity, refs 4b and 5c; antibacterial activity, refs 1a, 3b, and 7; antifungal activity, ref 2; inhibition of epidermal growth factor, ref 6; inhibition of compound 48/80-induced histamine release, ref 8; antimalarial activity, ref 7; anticancer properties, ref 1
    • Chemokine receptor antagonist activity, ref 1c; antiviral activity, refs 4b and 5c; antibacterial activity, refs 1a, 3b, and 7; antifungal activity, ref 2; inhibition of epidermal growth factor, ref 6; inhibition of compound 48/80-induced histamine release, ref 8; antimalarial activity, ref 7; anticancer properties, ref 1.
  • 25
    • 0037156593 scopus 로고    scopus 로고
    • For recent advances in the synthesis of diketopiperazines, see
    • For recent advances in the synthesis of diketopiperazines, see: Dinsmore, C. J.; Beshore, D. C. Tetrahedron 2002, 58, 3297-3312.
    • (2002) Tetrahedron , vol.58 , pp. 3297-3312
    • Dinsmore, C.J.1    Beshore, D.C.2
  • 29
    • 64549161048 scopus 로고    scopus 로고
    • 2117-2120
    • 2117-2120.
  • 31
    • 37049076652 scopus 로고    scopus 로고
    • Chaloner, P. A; Langadianou, E.; Perera, S. A. R. J. Chem. Soc., Perkin Trans. 1 1991, 2731-2735.
    • Chaloner, P. A; Langadianou, E.; Perera, S. A. R. J. Chem. Soc., Perkin Trans. 1 1991, 2731-2735.
  • 32
    • 64549136612 scopus 로고    scopus 로고
    • Use of Z-1-bromo-2-ethoxyethene/t-BuLi, which had been successful in our model study (ref 10, gave a complex mixture. We also tried a zincate complex cf. ref 19, but this reaction was too slow at-78 °C to be useful and gave a poor yield at a higher temperature. For related observations, see
    • (a) Use of Z-1-bromo-2-ethoxyethene/t-BuLi, which had been successful in our model study (ref 10), gave a complex mixture. We also tried a zincate complex (cf. ref 19), but this reaction was too slow at-78 °C to be useful and gave a poor yield at a higher temperature. For related observations, see:
  • 35
    • 64549104164 scopus 로고    scopus 로고
    • C(4)H-C(5)H is 8.0 Hz, which corresponds closely to the value (7.7 Hz) in the natural product (ref 1b). The corresponding coupling constants for the two epimers of 4 are <3 and 7.8 Hz for cis and trans C(4) and C(5) hydrogens, respectively.
    • C(4)H-C(5)H is 8.0 Hz, which corresponds closely to the value (7.7 Hz) in the natural product (ref 1b). The corresponding coupling constants for the two epimers of 4 are <3 and 7.8 Hz for cis and trans C(4) and C(5) hydrogens, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.