메뉴 건너뛰기




Volumn 41, Issue 19, 1985, Pages 3943-3958

Radical-initiated polyolefinic cyclizations in linear triquinane synthesis. model studies and total synthesis of (±)-hirsutene

Author keywords

[No Author keywords available]

Indexed keywords

HIRSUTENE;

EID: 0022405113     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)97175-3     Document Type: Article
Times cited : (152)

References (97)
  • 1
    • 84910582711 scopus 로고    scopus 로고
    • Recipient of a Dreyfus Young Investigator Award, 1981-86. Eli Lilly Grantee, 1985-86. A fellow of the Alfred P. Sloan Foundation, 1985-87.
  • 40
    • 84910572669 scopus 로고    scopus 로고
    • Some exceptions include the approaches of Wender (refs. 2k, 50 and Greene, refs. 2g, 4).
  • 41
    • 84910540272 scopus 로고    scopus 로고
    • Some exceptions include the approaches of Little (refs. 2j, 6c) and Mehta (refs 2i, 6i).
  • 47
    • 84910580260 scopus 로고    scopus 로고
    • For use of a related reductive cyclization, see ref. 6g.
  • 48
    • 84910541258 scopus 로고    scopus 로고
    • For a summary of basic strategies of ring construction which have been employed, see ref. 30.
  • 49
    • 84910544930 scopus 로고    scopus 로고
    • The elegant routes of Little (2j, 6c), Wender (2k, 5c), and Mehta (2i, 6i) also involve multiple ring construction.Professor K. N. Houk and T.-C. Wu have also recently developed an elegant intramolecular [6 + 2] cycloaddition approach to linear triquinanes (in press).
  • 62
    • 49149145492 scopus 로고
    • For a review of the regiochemistry of allylic displacements, see
    • (1980) Tetrahedron , vol.36 , pp. 1901
    • Magid1
  • 63
    • 84910592193 scopus 로고    scopus 로고
    • n2-anti substitution.
  • 64
    • 0001551578 scopus 로고
    • Interesting contrasts are available for cuprate openings of related vinyl lactones, see:
    • (1981) J. Org. Chem. , vol.46 , pp. 2591
    • Grieco1    Srinivasan2
  • 74
    • 84910545044 scopus 로고    scopus 로고
    • 3 distance in cyclohexane. Beckwith, A. L. J.; Easton, C. J.; Lawrence, T.; Serelis, A. K. Aust. _J. Chem. (1983), _36, 545.
  • 75
    • 84910572448 scopus 로고    scopus 로고
    • Calculations by Prof. K. N. Houk and D. Spellmeyer (in press) have revealed a transition state strikingly similar to the Beckwith model. We are grateful to K. N. H. and D. S. for providing us this information prior to publication. Since the submission of this manuscript, a similar computational analysis by Beckwith has appeared. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron Lett. (1985), 26, 373.
  • 76
    • 84910531684 scopus 로고    scopus 로고
    • Difficulties in preparing the required Grignard reagent from 1-trimethylsilyl-4-bromobutyne and handling the sensitive 1-methyl-cyclopent-2-en-l-ol lead us to abandon route A; however, with proper modifications, we do feel that this would be a viable approach.
  • 79
    • 33847087776 scopus 로고
    • We thank Prof. T. Cohen for helpful advice on the reductive lithiation.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 6900
    • Cohen1    Matz2
  • 83
    • 0000361841 scopus 로고
    • Hex-5-ynyl radicals are useful for cyclizations. See refs. 10 and 17 also:, and references therein
    • (1984) J. Org. them. , vol.49 , pp. 1313
    • Clive1    Beaulieu2    Set3
  • 86
    • 0346811864 scopus 로고
    • While many methods are available for the synthesis of 2-methylcyclopentenone, see:, we found the method of Smith to be far superior to several others.
    • (1980) Synthesis , pp. 118
    • Funk1    Vollhardt2
  • 92
    • 84910575342 scopus 로고    scopus 로고
    • W. Lin, unpublished results from these laboratories.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.