Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2011(5): 755-758
DOI: 10.1055/s-0030-1258418
DOI: 10.1055/s-0030-1258418
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereoselective Formal Total Synthesis of (-)-Swainsonine from Garner’s Aldehyde
Further Information
Received
2 December 2010
Publication Date:
21 January 2011 (online)
Publication History
Publication Date:
21 January 2011 (online)
![](https://www.thieme-connect.de/media/synthesis/201105/lookinside/thumbnails/10.1055-s-0030-1258418-1.jpg)
Abstract
A simple and facile stereoselective formal total synthesis of (-)-swainsonine has been reported starting from Garner’s l-serine derived oxazolidine aldehyde. Our synthetic strategy involves stereoselective allylation and Still olefination as key intermediary reaction steps.
Key words
swainsonine - indium - allylation - Garner’s aldehyde - Still olefination - indolizidine alkaloid
-
1a
Watson AA.Fleet GWJ.Asano N.Molyneux RJ.Nash RJ. Phytochemistry 2001, 56: 265 -
1b
Asano N.Nash RJ.Molyneux RJ.Fleet GWJ. Tetrahedron: Asymmetry 2000, 11: 1645 -
1c
Hakansson AE.Ameijde AV.Gugleilmini L.Horne G.Nash RJ.Evinson EL.Kato A.Fleet GWJ. Tetrahedron: Asymmetry 2007, 18: 282 -
2a
Aoki K.Nakamura A.Ito S.Nezu U.Iwasaki T.Takahashi M.Kimura M.Terauchi Y. Diabetes Res. Clin. Pract. 2007, 78: 30 -
2b
Alfasano P.Pampin S.Estrada J.Rey JCR.Giraldo P.Sancho J.Pocovi M. Blood Cells Mol. Dis. 2005, 35: 268 -
3a
Guengerich FP.DiMari SJ.Broquist HP. J. Am. Chem. Soc. 1973, 95: 2055 -
3b
Schneider MJ.Ungemach FS.Broquist HP.Harris TM. Tetrahedron 1983, 39: 29 - From the fungus Metarhizium anisopliae:
-
3c
Hino M.Nakayama O.Tsurumi Y.Adachi K.Shibata T.Terano H.Kohsaka M.Aoki H.Imanaka H. J. Antibiot. 1985, 35: 926 -
3d
Patrick MS.Adlard MW.Keshavarz T. Biotechnol. Lett. 1995, 17: 433 - From the legume Swainsona canescens:
-
3e
Colegate SM.Dorling PR.Huxtable CR. Aust. J. Chem. 1979, 32: 2257 - From the locoweed Astragalus lentiginosus:
-
3f
Molyneux RJ.James LF. Science 1982, 216: 190 - From Weir vine:
-
3g
Molyneux RJ.McKenzie RA.O’Sullivan BM.Elbein AD. J. Nat. Prod. 1995, 58: 878 -
3h For a review of the synthesis
and biological activity of swainsonine and other glycosidase inhibitors,
see:
Nishimura Y. Studies in Natural Products Chemistry Vol. 10: . Elsevier; Amsterdam: 1992. p.495-583 - 4
Gellert E. J. Nat. Prod. 1982, 45: 50 - 5
Zhao H.Hans S.Cheng X.Mooto DR. J. Org. Chem. 2001, 66: 1761 - 6
Trost BM.Patterson DE. Chem. Eur. J. 1999, 5: 3279 - 7
Punniyamurthy T.Irie R.Katsuki T. Chirality 2000, 12: 464 - 8
Pearson WH.Hembre EJ. J. Org. Chem. 1996, 61: 7217 - 9
Pearson WH.Ren Y.Powers JD. Heterocycles 2002, 58: 421 - 10
De Vicente J.Arrayas RG.Canada J.Carretero JC. Synlett 2000, 53 - 11
Lindsay KB.Pyne SG. J. Org. Chem. 2002, 67: 7774 - 12
Buschmann N.Ruckert A.Blechert S. J. Org. Chem. 2002, 67: 4325 - 13
Dondoni A.Perrone D. Org. Synth. 2000, 77: 64 - 14
Paquette LA.Mitzel TM.Isaac MB.Crasto CF.Schomer WW. J. Org. Chem. 1997, 62: 4293 - 15
Lemke A.Buschleb M.Ducho C. Tetrahedron 2010, 66: 208 - 16
Dess DB.Martin JC. J. Am. Chem. Soc. 1991, 113: 7277 - 17
Still WC.Gennari C. Tetrahedron Lett. 1983, 24: 4405 - 18
Martin R.Murruzzu C.Pericas MA.Riera A. J. Org. Chem. 2005, 70: 2325 - 19
Flamant-Robin C.Wang Q.Chiaroni A.Sasaki N. A. Tetrahedron 2002, 58: 10475