Synthesis of acetogenins

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

549472, C07D30758, C07D30712

Patent

active

056774672

ABSTRACT:
A method for the synthesis of bis-tetrahydrofuranyl annonaceous acetogenins, including the natural products and analogs thereof, is provided which proceeds by the Pd-mediated coupling of a bis-tetrahydrofuranyl-subunit comprising a terminal alkyne, with a (C4)-hydroxybutenolide subunit comprising a terminal vinyl iodide, followed by selective reduction of the resulting enyne.

REFERENCES:
patent: 5587491 (1996-12-01), Hoye et al.
Hoye and Ye, J. Am. Chem. Soc., 118, pp. 1801-1802 1996.
K. I. Ahammadsahib, et al., "Mode of Action of Bullatacin: A potent antitumor and Pesticidal Annonaceous Acetogenin", Life Sci., 53, 1113-1120, (1993).
Andre Cave, et al., "Recent Advances in the Acetogenins of Annonaceae", Recent Advances in Phytochemistry, vol. 27, Phytochemical Potential of Tropical Plants, Chapter 8, Plenum Press, NY, 167-202, (1993).
Mauro Degli Esposti, et al., "Natural Substances (acetogenins) from the family Annonaceae are Powerful Inhibitors of Mitochondrial NADH dehydrogenase (Complex I)", Biochem. J., 301, 161-167, (1994).
Xin-ping Fang, et al., "Annonaceous Acetogenins: An Updated Review", Phytochemical Analysis, 4, 27-48, (1993).
Xin-ping Fang, et al., "Annonaceous Acetogenins: An Updated Review -Appendices", Phytochemical Analysis, 4, 49-67, (1993).
Xin-Ping Fang, et al., "Gigantetrocin and Gigantriocin: Two Novel Bioactive Annonaceous Acetogenins from Goniothalamus Giganteus", Heterocycles, 32, 11-17, (1991).
Bruno Figadere, et al., "Synthesis of 2,33-Dihydro-4-Oxo-Murisolin: Conjugate Addition of Primary Alkyl Iodides to a,b-Unsaturated Ketones", Tetrahedron Letters, 33, 5189-5192, (1992).
Zhe-Ming Gu, et al., "Annonaceous Acetogenins", Recent Advances in Phytochemistry, vol. 29, Phytochemistry of Medicinal Plants, J.T. Arnason et al., eds. Plenum Press, NY, 249-310, (1995).
Zhe-ming Gu, et al., "Bullacin: A New Cytotoxic Annonaceous Acetogenin from Anona Bullata", Heterocycles, 36, 2221-2228, (1993).
Thomas R. Hoye, et al., "An Efficient and Versatile Synthesis of the Bulenolide Subunit of 4-Hydroxylated Annonaceous Acetogenins", Tetrahedron Letters, 35, 7517-7520, (1994).
Thomas R. Hoye, et al., "On the Stereochemistry of the Bistetrahydrofuranyl Moiety of Uvaricin: Proton Chemical Shifts Can Play a Crucial Role in Complex Structure Determination", J. Am. Chem. Soc., 109, 4402-4403, (1987).
Thomas R. Hoye, et al., "Synthesis of (-) -Bullatacin: The Enantiomer of a Potent, Antitumor, 4-Hydroxylated, Annonaceous Acetogenin", Tetrahedron Letters, 34, 5043-5046, (1993).
Thomas R. Hoye, et al., "Synthesis of (+)-(15,16,19,20,23,24)-hexepi-Uvaricin: A Bis(tetrahydrofuranyl) Annonaceous Acetogenin Analogue", J. Am. Chem. Soc., 113, 9369-9371, (1991).
Thomas R. Hoye, et al., "Total Synthesis of the Potent Antitumor, bis-Tetrahydrofuranyl Annonaceous Acetogenins (+)-Asimicin and (+)-Bullatacin", Tetrahedron Letters, 36, 1981-1984, (1995).
Y.-H. Hui, et al., "Bullatacin and Bullatacinone: Two Highly Potent Bioactive Acetogenins from Annona Bullata", J. of Nat. Products, 52, 463-477, (1989).
Ulrich Koert, "Total Synthesis of (+)-Rolliniastatin I", Tetrahedron Letters, 35, 2517-2520, (1994).
Mark A. Lewis, et al., "Inhibition of Respiration at Site I by Asimicin, an Insecticidal Acetogenin of the Pawpaw, Asimina Triloba (Annonaceae)", Pesticide Biochemistry and Physiology, 45, 15-23, (1993).
Michael Londershausen, et al., "Molecular Mode of Action of Annonins", Pestic. Sci.33, 427-438, (1991).
Hidefumi Makabe, et al., "Total Synthesis of Solamin and Reticulatacin", J. Chem. Soc. Perkin Transactions 1,, 1975-1981, (1994).
D. James Morre, et al., "Mode of Action of Bullatacin, a Potent Antitumor Acetogenin: Inhibition of NADH Oxidase Activity of Hela and HL-60, but not Liver, Plasma Membranes", Life Sciences, 56, 343-348, (1995).
Hiroyudi Naito, et al., "The First Total Synthesis of (+)-Bullatacin, a Potent Antitumor Annonaceous Acetogenin, and (+)-(15,24)-bisepi-Bullatacin", J. Org. Chem., 60, 4419-4427, (1995).
Sunil Raynayake, et al., "Parvifloracin and Parviflorin: cytotoxic bistetrahydrofuran acetogenins with 35 carbons from Asimina parviflora (Annonacene)", Can. J. Chem., 72, 287-293, (1994).
Matthew J. Rieser, et al., "Determination of Absolute Configuration of Stereogenic Carbinol Centers in Annonaceous Acetogenins by 1H-and 19F-NMR Analysis of Mosher Ester Derivatives", J. Am. Chem. Soc., 114, 10203-10213, (1992).
J. Kent Rupprecht, et al., "Annonaceous Acetogenins: A Review", J. of Natural Products, 53, 237-278, (1990).
Barry M. Trost, et al., "A Concise Convergent Strategy to Acetogenins (+)-Solamin and Analogues", J. Am. Chem. Soc., 116, 7459-7460, (1994).
Zhu-Jun Yao, et al., "Total Synthesis of (10E,15R,16S,19S,20S,34R)-Corossoline", Tetrahedron Letters, 35, 157-160, (1994).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Synthesis of acetogenins does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of acetogenins, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of acetogenins will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1556674

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.