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Synthesis 2009(17): 2983-2991
DOI: 10.1055/s-0029-1216927
DOI: 10.1055/s-0029-1216927
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkFormal Synthesis of Salinosporamide A Starting from d-Glucose
Further Information
Received
19 July 2009
Publication Date:
07 August 2009 (online)
Publication History
Publication Date:
07 August 2009 (online)
Abstract
A formal synthesis of salinosporamide A is described. The tertiary alcohol function in salinosporamide A was stereoselectively generated via the substrate control by the reaction of a cyclic ketone derived from d-glucose with Me3Al, and subsequent Overman rearrangement of an allylic trichloroacetimidate effectively constructed the tetrasubstituted carbon with nitrogen. Formation of γ-lactam, followed by the introduction of a cyclohexenyl unit furnished the Corey’s intermediate of salinosporamide A.
Key words
stereoselective synthesis - carbohydrates - chiral pool - rearrangements - pericyclic reactions
- 1a
Feling RH.Buchanan GO.Mincer TJ.Kauffman CA.Jensen PR.Fenical W. Angew. Chem. Int. Ed. 2003, 42: 355 - 1b
Fenical W.Jensen PR.Palladino MA.Lam KS.Lloyd GK.Potts BC. Bioorg. Med. Chem. 2009, 17: 2175 - 2
Williams PG.Buchanan GO.Feling RH.Kauffman CA.Jensen PR.Fenical W. J. Org. Chem. 2005, 70: 6196 - 3a
Omura S.Fujimoto T.Otoguro K.Matsuzaki K.Moriguchi R.Tanaka H.Sasaki Y. J. Antibiot. 1991, 44: 113 - 3b
Omura S.Matsuzaki K.Fujimoto T.Kosuge K.Furuya T.Fujita S.Nakagawa A. J. Antibiot. 1991, 44: 117 - 4a
Fenteany G.Standaert RF.Lane WS.Choi S.Corey EJ.Schreiber SL. Science 1995, 268: 726 - 4b
Chauhan D.Catley L.Li G.Podar K.Hideshima T.Velankar M.Mitsiades C.Mitsiades N.Yasui H.Letai A.Ovaa H.Berkers C.Nicholson B.Chao T.-H.Neuteboom STC.Richardson P.Palladino MA.Anderson KC. Cancer Cell 2005, 8: 407 - 4c
Macherla VR.Mitchell SS.Manam RR.Reed KA.Chao T.-H.Nicholson B.Deyanat-Yadzdi G.Mai B.Jensen PR.Fenical W.Neuteboom STC.Lam KS.Palladino MA.Potts BCM. J. Med. Chem. 2005, 48: 3684 - 4d
Joazeiro CAP.Anderson KC.Hunter T. Cancer Res. 2006, 66: 7840 - 4e
Miller CP.Rudra S.Keating MJ.Wierda WG.Palladino M.Chandra J. Blood 2009, 113: 4289 - For comprehensive reviews on syntheses of lactacystin and omuralide, see:
- 5a
Corey EJ.Li W.-ZD. Chem. Pharm. Bull. 1999, 47: 1 - 5b
Masse CE.Morgan AJ.Adams J.Panek JS. Eur. J. Org. Chem. 2000, 2513 - 5c
Shibasaki M.Kanai M.Fukuda N. Chem. Asian J. 2007, 2: 20 - For the synthesis of salinosporamide A, see:
- 6a
Reddy LRR.Saravanan P.Corey EJ. J. Am. Chem. Soc. 2004, 126: 6230 - 6b
Endo A.Danishefsky SJ. J. Am. Chem. Soc. 2005, 127: 8298 - 6c
Reddy LRR.Fournier J.-F.Reddy BVS.Corey EJ. Org. Lett. 2005, 7: 2699 - 6d
Mulholland NP.Pattenden G.Walters IAS. Org. Biomol. Chem. 2006, 4: 2845 - 6e
Caubert V.Langlois N. Tetrahedron Lett. 2006, 47: 4473 - 6f
Caubert V.Massé J.Retailleau P.Langlois N. Tetrahedron Lett. 2007, 48: 381 - 6g
Ma G.Nguyen H.Romo D. Org. Lett. 2007, 9: 2143 - 6h
Ling T.Macherla VR.Manam RR.McArthur KA.Potts BCM. Org. Lett. 2007, 9: 2289 - 6i
Mulholland NP.Pattenden G.Walters IAS. Org. Biomol. Chem. 2008, 6: 2782 - 6j
Takahashi K.Midori M.Kawano K.Ishihara J.Hatakeyama S. Angew. Chem. Int. Ed. 2008, 47: 6244 - 6k
Margalef IV.Rupnicki L.Lam HW. Tetrahedron 2008, 64: 7896 - 6l
Mosey RA.Tebe JJ. Tetrahedron Lett. 2009, 50: 295 - 6m
Struble JR.Bode JW. Tetrahedron 2009, 65: 4957 - 7a
Chida N.Takeoka J.Tsutsumi N.Ogawa S. J. Chem. Soc., Chem. Commun. 1995, 793 - 7b
Chida N.Takeoka J.Ando K.Tsutsumi N.Ogawa S. Tetrahedron 1997, 53: 16287 - 7c
Oishi T.Ando K.Chida N. Chem. Commun. 2001, 1932 - 7d
Oishi T.Ando K.Inomiya K.Sato H.Iida M.Chida N. Org. Lett. 2002, 4: 151 - 7e
Oishi T.Ando K.Inomiya K.Sato H.Iida M.Chida N. Bull. Chem. Soc. Jpn. 2002, 75: 1927 - For excellent reviews on Overman rearrangement and related reactions, see:
- 8a
Overman LE.Carpenter NE. In Organic Reactions Vol. 66:Overman LE. Wiley; New York: 2005. p.1 - 8b
Overman LE. Acc. Chem. Res. 1980, 13: 218 - 8c
Overman LE. Angew. Chem., Int. Ed. Engl. 1984, 23: 579 - For recent reports on the syntheses of natural products and related compounds utilizing Overman rearrangement, see:
- 9a
Imaoka T.Iwamoto O.Noguchi K.Nagasawa K. Angew. Chem. Int. Ed. 2009, 48: 3799 - 9b
Hama N.Matsuda T.Sato T.Chida N. Org. Lett. 2009, 11: 2687 - 9c
Dickson DP.Wardrop DJ. Org. Lett. 2009, 11: 1341 - 9d
Momose T.Hama N.Higashino C.Sato H.Chida N. Tetrahedron Lett. 2008, 49: 1376 - 9e
Sato H.Sato K.Iida M.Yamanaka H.Oishi T.Chida N. Tetrahedron Lett. 2008, 49: 1943 - 9f
Matveenko M.Kokas OJ.Banwell MG.Willis AC. Org. Lett. 2007, 9: 3683 - 9g
Hakansson AE.Palmelund A.Holm H.Madsen R. Chem. Eur. J. 2006, 12: 3243 - 9h
Tsujimoto T.Nishikawa T.Urabe D.Isobe M. Synlett 2005, 433 - 9i
Sato H.Maeba T.Yanase R.Yamaji-Hasegawa A.Kobayashi T.Chida N. J. Antibiot. 2005, 58: 37 - 9j
Nishikawa T.Urabe D.Yoshida K.Iwabuchi T.Asai M.Isobe M. Chem. Eur. J. 2004, 10: 452 - 9k
Ohyabu N.Nishikawa T.Isobe M. J. Am. Chem. Soc. 2003, 125: 8798 - 10a
Rosenthal A.Nguyen LB. J. Org. Chem. 1969, 34: 1029 - 10b
Fleet GWJ.James K.Lunn RJ.Mathews CJ. Tetrahedron Lett. 1986, 27: 3057 - 11
Schmidt RR.Kinzy W. In Advances in Carbohydrate Chemistry and Biochemistry Vol. 50:Horton D. Academic Press; San Diego: 1994. p.21 - 12
Albright JD.Goldman L. J. Am. Chem. Soc. 1965, 87: 4214 - 13
Sridhar M.Kumar BA.Narender R. Tetrahedron Lett. 1998, 39: 2847 - 14a
Nishikawa T.Asai M.Ohyabu N.Isobe M. J. Org. Chem. 1998, 63: 188 - 14b
Cho C.Lim Y.Lee K.Jung I.Yoon M. Synth. Commun. 2000, 30: 1643 - 15a
Pappo R.Allen DS.Lemieux RU.Johnson WS. J. Org. Chem. 1956, 21: 478 - 15b
Yu W.Mei Y.Kang Y.Hua Z.Jin Z. Org. Lett. 2004, 6: 3217