Total synthesis of salinosporamide A and analogs thereof

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

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C548S453000

Reexamination Certificate

active

08067616

ABSTRACT:
The present invention relates to certain compounds and to methods for the preparation of certain compounds that can be used in the fields of chemistry and medicine. Specifically, described herein are methods for the preparation of various compounds and intermediates, and the compounds and intermediates themselves. More specifically, described herein are methods for synthesizing Salinosporamide A and its analogs from a compound of formula (V).

REFERENCES:
patent: 7144723 (2006-12-01), Fenical et al.
patent: 7176232 (2007-02-01), Fenical et al.
patent: 7176233 (2007-02-01), Fenical et al.
patent: 7179834 (2007-02-01), Fenical et al.
patent: 7183417 (2007-02-01), Corey
patent: 7276530 (2007-10-01), Potts et al.
patent: 7371875 (2008-05-01), Xiao et al.
patent: 7465720 (2008-12-01), Corey et al.
patent: 7511156 (2009-03-01), Corey
patent: 7544814 (2009-06-01), Potts et al.
patent: 7579371 (2009-08-01), Palladino et al.
patent: 7635712 (2009-12-01), Fenical et al.
patent: 7691896 (2010-04-01), Myers et al.
patent: 7842814 (2010-11-01), Ling et al.
patent: 2005/0049294 (2005-03-01), Palladino et al.
patent: 2005/0228186 (2005-10-01), Corey
patent: 2006/0264495 (2006-11-01), Palladino et al.
patent: 2006/0287520 (2006-12-01), Danishefsky et al.
patent: 2007/0004676 (2007-01-01), Palladino et al.
patent: 2008/0070273 (2008-03-01), Fenical et al.
patent: 2009/0035390 (2009-02-01), Anderson et al.
patent: 2009/0069401 (2009-03-01), Fenical et al.
patent: 2009/0182027 (2009-07-01), Palladino et al.
patent: 2009/0197937 (2009-08-01), Fenical et al.
patent: 2009/0234137 (2009-09-01), Ling et al.
patent: 2009/0298906 (2009-12-01), Macherla et al.
patent: 2010/0144826 (2010-06-01), Fenical et al.
patent: WO 96/32105 (1996-10-01), None
patent: WO 99/09006 (1999-02-01), None
patent: WO 99/15183 (1999-04-01), None
patent: WO 2004/071382 (2004-08-01), None
patent: WO 2005/002572 (2005-01-01), None
patent: WO 2005/099687 (2005-10-01), None
patent: WO 2005/113558 (2005-12-01), None
patent: WO 2006/005551 (2006-01-01), None
patent: WO 2006/028525 (2006-03-01), None
patent: WO 2006/060676 (2006-06-01), None
patent: WO 2006/060809 (2006-06-01), None
patent: WO 2006/118973 (2006-11-01), None
patent: WO 2007/021897 (2007-02-01), None
patent: WO 2007/033039 (2007-03-01), None
patent: WO 2007/117591 (2007-10-01), None
patent: WO 2009/140287 (2009-11-01), None
Definition of “aminal,” IUPAC Compendium of Chemical Terminology 2nd Edition (1997).
Caubert et al. (Tetrahedron Letters, vol. 47, Issue 26, Jun. 26, 2006, pp. 4473-4475).
Fukuda et al. “Total Synthesis of Salinsporamide A” (2008) 10(19):4239-42.
Ling et al., “Concise Formal Synthesis of (−)-Salinosporamide A (Marizomib) Using a Regio- and Stereoselective Epoxidation and Reductive Oxirane Ring-Opening Strategy” J. Org. Chem. (2010) 75(11):3882-5.
Margalef, et al, “Formal Synthesis of Salinosporamide A Using a Nickel-catalyzed Reductive Aldol Cyclization-lactonization as a Key Step,”, Tetrahedron, (2008) 64(34):7896-7901.
Momose et al. “Formal Synthesis of Salinosporamide A Starting from D-Glucose” (2009) Synthesis, 17:2983-2991.
Mosey et al, “New Synthetic Route to Access (±) Salinosporamide A via an Oxazolone-Mediated Ene-Type Reaction” Tetrahedron Letters (2009) 50:295-7.
Struble et al., “Formal Synthesis of Salinosporamide Aj via NHC-Catalyzed Intramolecular Lactonization” Tetrahedron (2009) 65:4957-67.
Takahashi, et al., “Entry of Heterocycles Based on Indium Catalyzed Conia-Ene Reactions: Asymmetric Synthesis of (−)-Salinosporamide A” Angew. Chemie. Int. Ed., (2008) 47:1-4.
International Search Report and Written Opinion dated Sep. 28, 2010 for PCT Application No. PCT/US2009/036376, Filed Mar. 6, 2009.
International Preliminary Report on Patenability dated Oct. 5, 2010 for PCT Application No. PCT/US2009/036376, Filed Mar. 6, 2009.
EFS of U.S. Appl. No. 11/697,689, filed Apr. 6, 2007.
EFS of U.S. Appl. No. 12/399,382, filed Mar. 6, 2009 as of Jan. 25, 2011.
EFS of U.S. Appl. No. 10/821,621, filed Apr. 9, 2004.
EFS of U.S. Appl. No. 11/539,648, filed Oct. 9, 2006.
EFS of U.S. Appl. No. 12/028,024, filed Feb. 8, 2008.
EFS of U.S. Appl. No. 11/224,589, filed Sep. 12, 2005.
Andrews, et al., “Highly Functionalised Pyroglutamates by Intramolecular Aldol Reactions: Towards the Pyroglutamate Skeleton of Oxazolomycin”, Synlett: Letters (1996) 612-614.
Andrews, et al., “Regioselective dieckmann cyclisations leading to enantiopure highly functionalised tetramic acid derivatives”, J. Chem. Soc., Perkin Trans. (1998) 1:223-235.
Caubert et al., “Stereoselective formal synthesis of the potent proteasome inhibitor: salinosporamide A” Tetrahedron Lett. (2007) 48 :381-4.
Caubert et al., “Studies toward the synthesis of salinosporamide A, a potent proteasome inhibitor” Tetrahedron Lett (2006) 47:4473-5.
Corey, et al., “An efficient tool synthesis of a new and highly active analog of lactacystin”, Tetrahedron Letters (1998) 39:7475-7478.
Endo, et al., “Total synthesis of salinosporamide A”, J. Am. Chem. Soc. (2005) 127:8298-8299 and S1-S23.
Hogan, et al., “Proteasome inhibition by a totally synthetic β-lactam related to salinosporamide A and omuralide”, J. Am. Chem. Soc. (2005) 127:15386-15387.
Kramer et al., “Organoboranes: XIX *. The Preparation and Some Unusual Chemistry of B-allyl Derivatives of 9-Borabicyclo[3.3.1]nonane” J. Organomet. Chem (1977) 132 :9-27.
Ling et al., “Enantioselective Total Synthesis of (−)-Salinosporamide A (NPI-0052)” Org. Lett (2007) 9:2289-92 & Supporting Information, pp. S1-S34.
Ma, et al., Concise total synthesis of (±)-salinosporamide A, (±)-cinnabaramide A, and derivatives via a bis-cyclization process: implications for a biosynthetic pathway?, Org. Lett., (2007) 9(11):2143-2146.
Manam et al. “Enantioselective enzymatic conversion of keto-salinosporamide to (−)-Salinosporamide A (NPI-0052)” Tetrahedron Lett (2007) 48 :2537-40.
Mulholland, et al., “A concise total synthesis of salinosporamide A”, Org. Biomol. Chem. (2006) 4:2845-2846.
Potts et al. “Generating a Generation of Proteasome Inhibitors: From Microbial Fermentation to Total Synthesis of Salinosporamide A (Marizomib) and Other Salinosporamides” Marine Drugs (2010) 8(4):835-80.
Reddy, et al., “A simple sterecontrolled synthesis of salinosporamide A”, J. Am. Chem. Soc. (2004) 126:6230-6231.
Reddy, et al., “An efficient, stereocontrolled synthesis of a potent omuralide-salinosporin hybrid for selective proteasome inhibition”, J. Am. Chem. Soc. (2005) 127:8974-8976.
Reddy, et al., “New synthetic route for the enantioselective total synthesis of salinosporamide A and biologically active analogues”, Org. Lett. (2005) 7(13): 2699-2701.
Seebach et al., “73. Structure and Reactivity of Five- and Siz-Ring N,N-, N,O-, and O,O-Acetals: A Lesson in Allylic 1,3-Strain (A1,3 Strain)” Hely Chim Acta (1992) 75:913-34.
Seebach et al., “Self-Regeneration of Stereocenters (SRS)-Applications, Limitations, and Abandonment of a Synthetic Principle” Angew Chem Int. Ed (1996) 35:2708-48.
Seebach, et al., “α-Alkylation of serine with self-reproduction of the center of chirality”, Tetrahedron Letters (1984) 25(24):2545-2548.
International Preliminary Report on Patenability dated Oct. 8, 2008 for PCT Application No. PCT/US2007/008562, Filed Apr. 6, 2007.
International Search Report and Written Opinion dated Mar. 26, 2008, for PCT/US2007/008562, filed Apr. 6, 2007.

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

Total synthesis of salinosporamide A and analogs thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Total synthesis of salinosporamide A and analogs thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Total synthesis of salinosporamide A and analogs thereof will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4289363

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