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Volumn 53, Issue 9, 1997, Pages 3249-3268

Rational design, synthesis, and reactivity of lactendiynes, a new class of cyclic enediynes ortho-fused with the β-lactam ring

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINE DERIVATIVE; MACROCYCLIC COMPOUND;

EID: 0031550881     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00036-7     Document Type: Article
Times cited : (36)

References (58)
  • 2
    • 0011297163 scopus 로고
    • Danieli, B. Ed., Società Chimica Italiana, Roma
    • b) Banfi, L. in Seminars in Organic Synthesis, Danieli, B. Ed., Società Chimica Italiana, Roma, 1994.
    • (1994) Seminars in Organic Synthesis
    • Banfi, L.1
  • 20
    • 0011330849 scopus 로고    scopus 로고
    • note
    • 8 independently prepared some members of a second family of lactendiynes, represented by the general formula 2.
  • 23
    • 0011343634 scopus 로고    scopus 로고
    • note
    • 1/2 is known (ref. 4b)]. Our results showed for cycloaromatization of compounds 1 a ΔSE about 17 Kcal/mol higher than the one calculated for the model reaction.
  • 39
    • 0011291732 scopus 로고    scopus 로고
    • note
    • 18. Alcohol 14 was unstable in the dry state, forming unsoluble solid materials. On the contrary, both 13 and 15 were stable at -20°C for several weeks.
  • 43
    • 0011330573 scopus 로고    scopus 로고
    • ref. 4c
    • d) ref. 4c.
  • 45
    • 0011336486 scopus 로고    scopus 로고
    • note
    • 21. Although the yield of the direct conversion of 12 into 13 (Scheme 2) was in several instances good, in other cases, for reasons not yet understood, the reaction stopped at low conversion and the recovery of both product and substrate was low. For this reason, we later preferred, in the synthesis of unprotected derivatives (see Schemes 4,6), a two step sequence, involving desilylation followed by reacton with the complex iodine-morpholine.
  • 46
    • 0011343637 scopus 로고    scopus 로고
    • note
    • 1/2 of few minutes at 50°C was predicted.
  • 48
    • 0011299935 scopus 로고    scopus 로고
    • note
    • 24. A similar behaviour was experienced by Ohno on a PMB protected azetidinone: se ref. 11a.
  • 52
    • 0011336487 scopus 로고    scopus 로고
    • note
    • 27. The last step for the synthesis of 7 required expensive 2,2'-dipyridyl disulfide as coupling agent. Attempts to replace it with other cheaper coupling reagents were unsuccessful. Moreover, separation of 7 from 2-pyridylthiol was not trivial requiring careful silica gel chromatography.
  • 56
    • 0011330574 scopus 로고    scopus 로고
    • note
    • 31. It is worth noting that, while 14 (note 18) tended to polymerize in the dry state, 46 proved to be more stable and was recovered intact after several days in freezer.
  • 57
    • 0011373053 scopus 로고    scopus 로고
    • note
    • 3OD alone, the peaks were badly resolved.
  • 58
    • 0011343638 scopus 로고    scopus 로고
    • note
    • 33. These compounds failed to elute in GC at temperatures up to 280°C, because of their too low volatility. or of their low thermal stability.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.