ScienceDirect - Tetrahedron Letters : Oxidative coupling. : : II. The total synthesis of enterolactone

Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 127-130

Result list | previous < 2 of 36 > next

Font Size:

Abstract - selected

References

PDF (219 K)

Article Toolbox

E-mail Article

Cited By

Save as Citation Alert

Set up a citation RSS feed (Opens new window)

Citation Feed

Export Citation

Add to my Quick Links

Bookmark and share in 2collab (opens in new window)

Request permission to reuse this article

Cited By in Scopus (11)

Related Articles in ScienceDirect

Synthesis of diarylbutanes from cordigerines and reinve...
Tetrahedron Letters

You are entitled to access the full text of this document

Synthesis of diarylbutanes from cordigerines and reinvestigation of their oxidative couplings in deoxyschizandrins. - An unusual formation of phenyltetralin lignans -
Tetrahedron Letters, Volume 28, Issue 43, 1987, Pages 5161-5164
Y. Landais, A. Lebrun, V. Lenain, J. -P. Robin

Abstract

Dibenzylbutanolide lignans including cordigerines were synthetized and transformed in the corresponding diarylbutane lignans which were submitted to non-phenolic oxidative coupling conditions by using RuO₂ or Tl₂O₃ in trifluoroacetic medium to give deoxyschizandrins. A concurrently aryl-benzyl coupling leads to the formation of the corresponding phenyltetralin of which the structure was confirmed by total synthesis.

PDF (283 K)

Total synthesis of (+/-)-11--methyl-caesalpin J and its...
Tetrahedron

Total synthesis of (±)-11--methyl-caesalpin J and its C-13 epimer
Tetrahedron, Volume 45, Issue 20, 1989, Pages 6361-6366
Gábor Blaskó, Geoffrey A. Cordell

Abstract

The biomimetic total syntheses of racemic 11-

-methyl-caesalpin J (9) and 13-epi-11-

-methyl-caesalpin J (10), via phenolic oxidative coupling of the accordingly substituted homoisoflavans 6 and 7, are described.

PDF (376 K)

Formation of 6,13-dimethyl-5,12-diazachrysene by oxidat...
Tetrahedron Letters

Formation of 6,13-dimethyl-5,12-diazachrysene by oxidative coupling of 2-methylindole followed by base-induced ring-expansion
Tetrahedron Letters, Volume 39, Issue 23, 4 June 1998, Pages 4119-4122
J. Bergman, S. Bergman, J. -O. Lindström

Abstract

Oxidative coupling of 2-methylindole with FeCl₃ gave, in addition to a trimeric coupling product, also the ring-expanded product 6,13-dimethyl-5,12-diazachrysene.

PDF (160 K)

Iodine oxidative coupling of diene and triene-diolates ...
Tetrahedron

Iodine oxidative coupling of diene and triene-diolates of unsaturated carboxylic acids.
Tetrahedron, Volume 47, Issues 10-11, 11 March 1991, Pages 1997-2004
M. J. Aurell, S. Gil, M. Parra, A. Tortajada, R. Mestres

Abstract

Oxidative Coupling of the dianions of unsaturated carboxylic acids 1, and 4 with iodine, which provides a convenient and facile preparation of γ,γ and var epsilon

-dicarboxylic acids 2 and 5, apparently occurs through SET substitution of intermediate iodo-carboxylates.

PDF (462 K)

Fe2O3/LiCl catalysts for methane activation
Materials Letters

Fe₂O₃/LiCl catalysts for methane activation
Materials Letters, Volume 27, Issues 4-5, July 1996, Pages 129-133
D. Lazarov, V. Rives, R. Klissurska, I. Mitov, D. Klissurki

Abstract

Oxidative coupling of methane (OCM) has been studied on a LiCl-promoted Fe₂O₃ catalyst (atomic ratio Fe:Li = 4:1). LiFe₅O₈ exists in the fresh catalyst calcined at 1073 K. α-Fe₂O₃ is reduced to non-stoichiometric magnetite, and LiFe₅O₈ existing in the fresh catalyst calcined at 1073 K is partially reduced to Fe₃O₄ and converted to LiFeO₂. Low selectivity in OCM to ethane and ethylene has been attributed to consumption of the LiCl promoter in a bulk interaction, resulting in the formation of new ferrite phases, which favour the destructive oxidation of methane.

PDF (367 K)

View More Related Articles

View Record in Scopus

doi:10.1016/S0040-4039(00)83958-1

Oxidative coupling. : II. The total synthesis of enterolactone

J. L. Belletire, ^* and S. L. Fremont

Department of Chemistry University of Cincinnati Cincinnati, Ohio 45221 U.S.A.

Received 16 September 1985.

Available online 8 March 2001.

Abstract

Oxidative coupling of 3-methoxyhydrocinnamic acid dianion with molecular iodine forms the key step in an efficient synthesis of enterolactone.

References

S.R. Stitch, J.K. Toumba, M.B. Groen, C.W. Funke, J. Leemhuis, J. Vink and G.F. Woods Nature (London) 287 (1980), p. 738. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (53)
K.D.R. Setchell, A.M. Lawson, F.L. Mitchell, H. Adlercreutz, D.N. Kirk and M. Axelson Nature (London) 287 (1980), p. 740. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (102)

K.D.R. Setchell, S.P. Borriello, H. Gordon, A.M. Lawson, R. Harkness, D.M.L. Morgan, D.N. Kirk, H. Adlercreutz, L.C. Andersen and M. Axelson Lancet ii (1981), p. 4. Article | PDF (545 K) | View Record in Scopus | Cited By in Scopus (128)
M. Axelson, J. Sjovall, B.E. Gustaffson and K.D.R. Setchell Nature (London) 298 (1982), p. 659. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (177)

K.D.R. Setchell, A.M. Lawson, M. Axelson and H. Adlercreutz Res. Steroids 9 (1981), p. 207.

A.P. Walters and J.T.J. Knowler Reprod. Fertil. 66 (1982), p. 379.

G. Cooley, R.D. Farrant, D.N. Kirk, S. Patel, S. Wynn, M.J. Buckingham, G.E. Hawkes, M.B. Hursthouse, A.M.R. Galas, A.M. Lawson and K.D.R. Setchell J. Chem. Soc. 2 (1984), p. 489 Perkin Trans. . Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (3)

G. Cooley, R.D. Farrant, D.N. Kirk and S. Wynn Tetrahedron Lett. 21 (1981), p. 349. Abstract | PDF (178 K) | View Record in Scopus | Cited By in Scopus (4)

M.B. Groen and J. Leemhuis Tetrahedron Lett. 21 (1980), p. 5043. Abstract | PDF (209 K) | View Record in Scopus | Cited By in Scopus (11)

K.K. Mahalanbis, M. Mumtaz and V. Snieckus Tetrahedron Lett. 23 (1982), p. 3975.

A. Pelter, P. Satyanarayana and R.S. Ward Tetrahedron Lett. 22 (1981), p. 1549. Abstract | PDF (140 K) | View Record in Scopus | Cited By in Scopus (6)
D.N. Kirk, L.M. McLaughlin, A.M. Lawson, K.D.R. Setchell and S.K. Patel J. Chem. Soc. 1 (1985), p. 35 Perkin Trans. . Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (4)

J.L. Belletire, E.G. Spletzer and A.R. Pinhas Tetrahedron Lett. 25 (1984), p. 5969. Abstract | PDF (263 K) | View Record in Scopus | Cited By in Scopus (22)

C.B.S. Rao Chemistry of Lignans, Andhra University Press, Waltair (1978).

S.A.M.T. Hussain, W.D. Ollis, C. Smith and J.F. Stoddart J. Chem. Soc. 1 (1975), p. 480 Perkin Trans. .

This problem was also noticed by M. B. Groen, private communication, 1985.

Y. Asana, T. Kamikawa and T. Tokoroyama Bull. Chem. Soc. Jpn. 49 (1976), p. 3232.
R.D. Haworth and D. Woodcock J. Chem. Soc. (1938), p. 1985. Full Text via CrossRef
R.D. Haworth and L. Wilson J. Chem. Soc. (1950), p. 71. Full Text via CrossRef

Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 127-130

Result list | previous < 2 of 36 > next

About ScienceDirect | Contact Us | Information for Advertisers | Terms & Conditions | Privacy Policy