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Tetrahedron
Volumn 51, Issue 30, 1995, Pages 8213-8230
Synthesis of saframycins. XI. Synthetic studies toward a total synthesis of safracin A
Author keywords

[No Author keywords available]
Indexed keywords

ANTIBIOTIC AGENT; SAFRACIN A; SAFRAMYCIN; UNCLASSIFIED DRUG;
EID: 0029040246     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00437-D     Document Type: Article
Times cited : (21)
References (37)
  • 9
    • 84916466674 scopus 로고    scopus 로고
    • Ikeda, Y.; Ogawa, H.; Matsuki, H.; Munakata, T.; Jpn. Kokai Tokkyo Koho 84 42382
  • 17
    • 84916470527 scopus 로고    scopus 로고
    • Reichenbach, H. Jpn. Kokai Tokkyo Koho 88 49092
  • 24
    • 0024447019 scopus 로고
    • Previously, we reported a mild, efficient dehydration/cyclization of an allylic alcohol substrate to give the corresponding (E)-1,5-imino-3-benzazocine with methanesulfonyl chloride and triethylamine in dichloromethane
    • (1989) J. Org. Chem. , vol.54 , pp. 5391-5395
    • Saito1    Yamauchi2    Nishioka3    Ida4    Kubo5
  • 25
    • 84916517158 scopus 로고    scopus 로고
    • However, on treating 7a under the same conditions at reflux, no cyclization product occurred. Instead, only an unstable polymeric material was obtained.
  • 26
    • 84916520720 scopus 로고    scopus 로고
    • Recently, Joule reported that an allylic alcohol iii can be quantitatively converted to the indeno[1.2-b] pyrazin-2-one iv in formic acid at room temperature for 1 h
  • 27
    • 37049082258 scopus 로고
    • Alternative synthesis of 6-(3-methoxybenzyl)pyrazin-2(1H)-one. Synthesis of indeno[1,2-b]pyrazin-2-ones. Crystal structures of 5-acetoxy-1-benzyl-4-tert-butoxycarbonyl-6-(3-methoxybenzylidene)piperazin-2-one, 1-benzyl-4-tert-butoxycarbonyl-7-methoxy-1,3,4,4a-tetrahydroindeno[1,2-b]pyrazin-2-one and 1-benzyl-4-tert-butoxycarbonyl-7-methoxy-1,3,4,9-tetrahydroindeno[1,2-b]pyrazin-2-one
    • (1993) Journal of the Chemical Society, Perkin Transactions 1 , vol.1 , pp. 1217-1224
    • Peters1    Beddoes2    Joule3
  • 28
    • 84916497012 scopus 로고    scopus 로고
    • 3 in ethanol at room temperature for 16 h followed by trifluoroacetic acid at room temperature for 20 h gave 28 in 53% overall yield; see Experimental section:
  • 30
    • 84916515197 scopus 로고    scopus 로고
    • Ikeda, Y.; Ogawa, H.; Matsuki, H.; Munakata, T.; Jpn. Kokai Tokkyo Koho 84 42382
  • 31
    • 84916489696 scopus 로고    scopus 로고
    • However, on treating 7a under the same conditions at reflux, no cyclization product occurred. Instead, only an unstable polymeric material was obtained.
  • 32
    • 84916505503 scopus 로고    scopus 로고
    • Recently, Joule reported that an allylic alcohol iii can be quantitatively converted to the indeno[1.2-b] pyrazin-2-one iv in formic acid at room temperature for 1 h
  • 33
    • 84916515712 scopus 로고    scopus 로고
    • 3 in ethanol at room temperature for 16 h followed by trifluoroacetic acid at room temperature for 20 h gave 28 in 53% overall yield; see Experimental section:
  • 34
    • 84916488866 scopus 로고    scopus 로고
    • 1H NMR spectrum of vi showed H-9 (δ 4.09) and H-14a (δ 2.84). 9a
  • 35
    • 84916518557 scopus 로고    scopus 로고
    • 1H NMR analysis. When H-10 (δ 6.29) was irradiated, nuclear Overhauser enchancement of the methylene protons at δ 3.35 and 3.80 was observed.
  • 37
    • 84916475134 scopus 로고    scopus 로고
    • A preliminary experiment for the partial demethylation of compound 31 was carried out under a variety of conditions; boron tribromide (1.5 equiv) gave 32 (55%), 33 (11%), and 31 (27% recovery); boron tribromide (2.5 equiv) gave 32 (37%) and 33 (31%); boron tribromide (5 equiv) gave only 33 (8%).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.