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 2010(16): 2841-2852
DOI: 10.1055/s-0030-1258151
DOI: 10.1055/s-0030-1258151
FEATUREARTICLE
© Georg Thieme Verlag
Stuttgart ˙ New York
Enantioselective Synthesis of (+)-Polyanthellin A via Cyclopropane-Aldehyde (3+2)-Annulation
Further Information
Received
4 June 2010
Publication Date:
07 July 2010 (online)
Publication History
Publication Date:
07 July 2010 (online)
Abstract
The asymmetric synthesis of the cladiellin diterpene natural product (+)-polyanthellin A is described. The core tetrahydrofuran was constructed using a stereospecific and stereoselective (3+2)-annulation of a donor-acceptor cyclopropane and a labile β-silyloxy aldehyde. These particular reactants necessitated the application of a new Lewis acid, MADNTf2 [(ArO)2AlNTf2], to avoid competitive elimination. Ring-closing metathesis was employed to form the oxonane ring at C3-C4 and give a functional group handle that could be elaborated to the natural product.
Key words
annulation - total synthesis - heterocycles - Lewis acids - ring opening
- 1
Stierle DB.Carte B.Faulkner DJ.Tagle B.Clardy J. J. Am. Chem. Soc. 1980, 102: 5088 - 2
Bernardelli P.Paquette LA. Heterocycles 1998, 49: 531 - 3
Rodriguez AD. Tetrahedron 1995, 51: 4571 - 4
Sung PJ.Chen MC. Heterocycles 2002, 57: 1705 - 5
MacMillan DWC.Overman LE. J. Am. Chem. Soc. 1995, 117: 10391 - 6
MacMillan DWC.Overman LE.Pennington LD. J. Am. Chem. Soc. 2001, 123: 9033 - 7
Ellis JM.Crimmins MT. Chem. Rev. 2008, 108: 5278 - 8
Overman LE.Pennington LD. Org. Lett. 2000, 2: 2683 - 9
Becker J.Bergander K.Fröhlich R.Hoppe D. Angew. Chem. Int. Ed. 2008, 47: 1654 - 10
Alam MJ.Sharma P.Zektzer AS.Martin GE.Ji X.van der Helm DJ. J. Org. Chem. 1989, 54: 1896 - 11
Sharma P.Alam MJ. J. Chem. Soc., Perkin Trans. 1 1988, 2537 -
12a
Kim H.Lee H.Kim J.Kim S.Kim D. J. Am. Chem. Soc. 2006, 128: 15851 -
12b
Molander GA.Czako B.St. Jean DJ. J. Org. Chem. 2006, 71: 1172 - For an initial communication from our laboratory, see:
-
12c
Campbell MJ.Johnson JS. J. Am. Chem. Soc. 2009, 131: 10370 - 13
Bowden BF.Coll JC.Vasilescu IM. Aust. J. Chem. 1989, 42: 1705 - 14
Ospina CA.Rodriguez AD.Ortega-Barria E.Capson TL. J. Nat. Prod. 2003, 66: 357 - 15
Pohlhaus PD.Johnson JS. J. Am. Chem. Soc. 2005, 127: 16014 - 16
Pohlhaus PD.Johnson JS. J. Org. Chem. 2005, 70: 1057 - 17 Pohlhaus P. D., Sanders S. D., Parsons A. T., Li W., Johnson J. S.; J. Am. Chem. Soc.; 2008, 130: 8642
- 18
Hagiwara H.Ono H.Hoshi T. Org. Synth. 2003, 80: 195 - 19
Mander LN.Sethi SP. Tetrahedron Lett. 1983, 24: 5425 - 20
Yang D.Gao Q.Lee C.-S.Cheung K.-K. Org. Lett. 2002, 4: 3271 - 21
Grieco PA.Gilman S.Nishizawa M. J. Org. Chem. 1976, 41: 1485 - 23 For a review of (3+n) cyclopropane
annulations in natural product synthesis, see:
Carson CA.Kerr MA. Chem. Soc. Rev. 2009, 38: 3051 - 24
Chi Y.Gellman SH. Org. Lett. 2005, 7: 4253 - 25
Chen K.Baran PS. Nature 2009, 459: 824 - 26
Klunder JM.Onami T.Sharpless KB. J. Org. Chem. 1989, 54: 1295 - 27
Hanson RM.Sharpless KB. J. Org. Chem. 1986, 51: 1922 - 28
Shao H.Zhu Q.Goodman M. J. Org. Chem. 1995, 60: 790 - 29
Tanner D.Somfai P. Tetrahedron 1986, 42: 5985 - 30
Kuehne ME.Bornmann WG.Marko I.Qin Y.LeBoulluec KL.Frasier DA.Xu F.Mulamba T.Ensinger CL.Borman LS.Huot AE.Exon C.Bizzarro FT.Cheung JB.Bane SL. Org. Biomol. Chem. 2003, 1: 2120 - 31
Sapeta K.Kerr MA. Org. Lett. 2009, 11: 2081 - 32
Canales E.Prasad KG.Soderquist JA. J. Am. Chem. Soc. 2005, 127: 11572 - 33
Casolari S.D’Addari D.Tagliavini E. Org. Lett. 1999, 1: 1061 - 34
Wu TR.Shen L.Chong JM. Org. Lett. 2004, 6: 2701 - 35
Moller R.Engel N.Stelich W. Synthesis 1978, 620 - 36
Qiao C.Jeon H.-B.Sayre LM. J. Am. Chem. Soc. 2004, 126: 8038 - 37
Boxer MB.Yamamoto H. Org. Lett. 2005, 7: 3127 - 38
Covell DJ.White MC. Angew. Chem. Int. Ed. 2008, 47: 6448 - 39
Yu J.-Q.Corey EJ. Org. Lett. 2002, 4: 2727 - 40
Fousteris MA.Koutsourea AI.Nikolaropoulos SS.Riahi A.Muzart J. J. Mol. Catal. A: Chem. 2006, 250: 70 - 41
Choi H.Doyle MP. Org. Lett. 2007, 9: 5349 - 42
Schmidt B. J. Org. Chem. 2004, 69: 7672 - 43
Corey EJ.Suggs JW. J. Org. Chem. 1973, 38: 3224 - 44
Clark JS.Kettle JG. Tetrahedron Lett. 1997, 38: 127 - 45
Ikeda Y.Ukai J.Ikeda N.Yamamoto H. Tetrahedron 1987, 43: 723 - 46
Corey EJ.Myers AG. Tetrahedron Lett. 1984, 25: 3559 - 47
Joe D.Overman LE. Tetrahedron Lett. 1997, 38: 8635 - 48
Hoye TR.Jeffrey CS.Tennakoon MA.Wang J.Zhao H. J. Am. Chem. Soc. 2004, 126: 10210 - 49
Nosse B.Schall A.Jeong WB.Reiser O. Adv. Synth. Catal. 2005, 347: 1869 - 50
Grela K.Harutyunyan S.Michrowska A. Angew. Chem. Int. Ed. 2002, 41: 4038 - 51
Michrowska A.Bujok R.Harutyunyan S.Sashuk V.Dolgonos G.Grela K. J. Am. Chem. Soc. 2004, 126: 9318 - 52
Yates MH. Tetrahedron Lett. 1997, 38: 2813 - 53
Brown HC.Desai MC.Jadhav PK. J. Org. Chem. 1982, 47: 5065 - 54
Hochlowski JE.Faulkner DJ. Tetrahedron Lett. 1980, 21: 4055 - 55
Kelly BD.Allen JM.Tundel RE.Lambert TH. Org. Lett. 2009, 11: 1381 - 56
Schuster C.Broeker J.Knollmueller M.Gaertner P. Tetrahedron: Asymmetry 2005, 16: 2631 - 57
Murray RW.Singh M. Org. Synth. 1998, 74: 91 - 58
Alaimo PJ.Peters DW.Arnold J.Bergman RG.
J. Chem. Educ. 2001, 78: 64
References
X-ray crystallography was performed by Dr. Peter White. CCDC 773310 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.