메뉴 건너뛰기




Volumn 128, Issue 43, 2006, Pages 14185-14191

A total synthesis of xestodecalactone A and proof of its absolute stereochemistry: Interesting observations on dienophilic control with 1,3-disubstituted nonequivalent allenes

Author keywords

[No Author keywords available]

Indexed keywords

ASSEMBLY; KETONES; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 33750479505     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064270e     Document Type: Article
Times cited : (67)

References (72)
  • 13
    • 0017761198 scopus 로고
    • For selected references of other syntheses of lasiodiplodin: (a) Gerlach, H.; Thalmann, A. Helv. Chim. Acta 1977, 60, 2866.
    • (1977) Helv. Chim. Acta , vol.60 , pp. 2866
    • Gerlach, H.1    Thalmann, A.2
  • 27
  • 35
    • 0031875042 scopus 로고    scopus 로고
    • (d) For AAG-Hsp90 binding (AAG, a derivative of geldanamycin, is the first Hsp90 inhibitor to enter clinical trials): Schulte, T. W.; Neckers, L. M. Cancer Chemother. Pharmacol. 1998, 42, 273.
    • (1998) Cancer Chemother. Pharmacol. , vol.42 , pp. 273
    • Schulte, T.W.1    Neckers, L.M.2
  • 41
    • 0002428769 scopus 로고    scopus 로고
    • For reviews on retro Diels-Alder reactions: (a) Rickborn, B. Org. React. 1998, 52, 1.
    • (1998) Org. React. , vol.52 , pp. 1
    • Rickborn, B.1
  • 44
    • 33750468550 scopus 로고    scopus 로고
    • Reference 14
    • For examples of related retro-Diels-Alder reactions: (d) Reference 14.
  • 55
    • 33750475443 scopus 로고    scopus 로고
    • JP 2000287697 A2 20001017 (Japanese)
    • Hanasaki, K.; Kamigaito, T.; JP 2000287697 A2 20001017 (Japanese).
    • Hanasaki, K.1    Kamigaito, T.2
  • 58
  • 60
    • 0032483411 scopus 로고    scopus 로고
    • For preparation of allene 35: In a two-step process, dehydroacetic acid was unraveled to methyl 3,5-dioxohexanoate (preparation see: Solladie, G.; Colobert, F.; Denni, D. Tetrahedron: Asymmetry 1998, 9, 3081)
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 3081
    • Solladie, G.1    Colobert, F.2    Denni, D.3
  • 61
    • 0032572870 scopus 로고    scopus 로고
    • followed by treatment with freshly prepared DMC (generated from 1,3-dimethyl-2-imidazolidinone) providing allene 35 (DMC protocol: Node, M.; Fujiwara, T.; Ichihashi, S.; Nishide, K. Tetrahedron Lett. 1998, 39, 6331). For preparation of allene 42: Similarly, commercially available tert- butylacetoacetate was extended to tert-butyl 3,5-dioxohexanoate, and treatment with DMC furnished allene 42.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6331
    • Node, M.1    Fujiwara, T.2    Ichihashi, S.3    Nishide, K.4
  • 62
    • 33750444822 scopus 로고    scopus 로고
    • note
    • The inseparable mixture of 36/37 was selectively reduced (sodium borohydride) to give alcohol 37A and unreacted isomer 36. On the basis of its proton NMR spectroscopic pattern (the benzylic methylene protons were each a dd, and the geminal proton of alcohol was a complex multiplet), alcohol 37A was determined to arise from reduction of 37. The alcohol was oxidized (TPAP/NMO) back to ketone 37. It was then readily discernible which proton NMR peak of the Diels-Alder adducts mixture belong to which product, particularly the benzylic methylene, methyl ketone (acetyl), and methyl ester. These three distinct peaks in the NMR were subsequently used to determine the ratios of Diels-Alder products. (Equation Presented)
  • 63
    • 0002616937 scopus 로고
    • For seminal discussions on the mechanism of the Diels-Alder reaction, concerted or stepwise: (a) Woodward, R. B.; Katz, R. B. Tetrahedron 1959, 5, 70.
    • (1959) Tetrahedron , vol.5 , pp. 70
    • Woodward, R.B.1    Katz, R.B.2
  • 66
    • 33750457882 scopus 로고    scopus 로고
    • Unpublished results by T. Yoshino
    • Unpublished results by T. Yoshino.
  • 72
    • 33750455696 scopus 로고    scopus 로고
    • note
    • The synthesis of diene 64 is described in Supporting Information. Cycloaddition of dienophile 62 and siloxyl diene was unsuccessful.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.