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Tetrahedron Letters
Volumn 12, Issue 38, 1971, Pages 3521-3524
Total synthesis of dl-illudol
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Indexed keywords

EID: 49649149081     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(01)97221-1     Document Type: Article
Times cited : (38)
References (11)
  • 3
    • 84918225695 scopus 로고    scopus 로고
    • The absolute structures of hirsutic acid (F.W. Comer, F. McCapra, I.H. Qureshi and A.I. Scott, Tetrahedron 23, 4761, 1967)) and of fomannosin (J.A. Kepler, M.E. Wall, J.E. Mason, C. Basset, A.T. McPhail and G.A. Sim, J. Am. Chem. Soc., 89, 1260 (1967)) have been shown as i and ii respectively. If the absolute configuration at the A/B ring juncture of illudol 1 is identical with that of i and the absolute configuration at the quarternary carbon atom on the four-membered ring is common in i and ii, illudol should have a cis-anti carbon framework of 2.
  • 4
    • 84918225694 scopus 로고    scopus 로고
    • Reasonable ir and nmr spectra have been obtained for this compound.
  • 5
    • 84918225693 scopus 로고    scopus 로고
    • The molecular formula of this compound has been confirmed by elementary analysis and by mass spectrometry.
  • 7
    • 84918225692 scopus 로고    scopus 로고
    • All the nmr spectra were taken in deuterochloroform solution with TMS as internal standard.
  • 8
    • 84918225691 scopus 로고    scopus 로고
    • The molecular formula of this compound has been ascertained by exact mass spectrometry.
  • 9
    • 84918225690 scopus 로고    scopus 로고
    • Inspection of molecular models indicates that in this case the cis-perhydroindenone structure 8 is more stable than the trans isomer, because of the flattened conformation of the six-membered ring.
  • 10
    • 84918225689 scopus 로고    scopus 로고
    • The hydroxyl/angular methyl cis structure is assigned for the major product 9, since attack of the reducing reagent from the less hindered side of 8 is clearly more favorable.
  • 11
    • 84918225688 scopus 로고    scopus 로고
    • The configuration of newly formed hydroxy group is cis relative to the angular methyl group by the similar reason as in the footnote 9.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.