Biomimetic synthesis of the neolignans kadsurenone, denudatin B, O- methyl-liliflodione, and liliflol B

Tetrahedron Letters

Volumn 40, Issue 30, 1999, Pages 5443-5447

  Horne, David A ^a   Yakushijin, Kenichi ^a   Büchi, George ^a,b  

^a OREGON STATE UNIVERSITY   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DENUDATIN B; KADSURENONE; LILIFLOL B; NEOLIGNAN; O METHYL LILIFLODIONE; THROMBOCYTE ACTIVATING FACTOR ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0033166756     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01063-1     Document Type: Article

References (27)

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6. (b) Gottlieb, O. R. Phytochemistry 1972, 11, 1537. For a more recent discussion on neolignan biosynthesis, see: Angle, S. R.; Turnbull, K. D. J. Am. Chem. Soc. 1990, 112, 3698.
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13. 4: C, 64.27; H, 7.19; found: C, 64.06; H, 7.21.
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16. 3): δ 3.10 (d, J=5.5 Hz, 2H), 3.40 (s, 6H), 3.81 (s, 3H), 5.16 (m, 2H), 5.43 (s, 1H), 5.89 (m, 1H), 6.18 (t, J=1.5 Hz, 1H).
17. For syntheses of denudatin B, see: (a) Shizuri, Y.; Yamamura, S. Tetrahedron Lett. 1983, 24, 5011.
18. (b) Ponpipom, M. M.; Yue, B. Z.; Bugianesi, R. L.; Briiker, D. R.; Chang, M. N.; Shen, T. Y. Tetrahedron Lett. 1986, 27, 309.
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21. (e) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O.; Ray, J. E. J. Org. Chem. 1994, 59, 6567.
22. 3): δ 1.07 (d, J=6.0 Hz, 3H), 2.47 (m, 2H), 3.12 (m, 2H), 3.52 (s, 1H), 3.64 (s, 3H), 3.85 (s, 6H), 5.19 (m, 2H), 5.87 (m, 1H), 6.59 (d, J=2.7 Hz, 1H), 6.66 (dd, J=8.8, 2.7 Hz, 1H), 6.79 (d, J=8.8 Hz, 1H), 7.05(s, 1H).
23. De Alvarenga, M. A.; Brocksom, U.; Gottlieb, O. R.; Yoshida, M. J. Chem. Soc., Chem. Comm. 1978, 831.
24. Engler, T. A.; Combrink, K. D.; Ray, J. E. J. Am. Chem. Soc. 1988, 110, 7931.
25. A related approach using p-quinol model compounds has been reported: Mortlock, S. V.; Seckington, J. K.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1988, 2305.
26. The major product (40-50%) resulting from the acid-facilitated reaction of p-quinol ether 8 and propenylbenzene 11E has been tentatively assigned the spiro-dienone (futoenone-like) structure shown below as a mixture of diastereomers. This is a result of olefin addition γ to the carbonyl which is the site of initial ionization in 8. In the case of o-quinone ketal 10 which affords significantly higher yields of hydrobenzofuran and bicyclooctanone products, initial ionization takes place α to the carbonyl (the requisite site of olefin addition). (formula presented)
27. See Ref. 11e and references cited therein.