RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2010(2): 247-249
DOI: 10.1055/s-0029-1218572
DOI: 10.1055/s-0029-1218572
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Stereocontrolled Synthesis of (±)-Ptilocaulin via a Rh(I)-Catalyzed Intramolecular [4+2] Cycloaddition
Weitere Informationen
Received
9 September 2009
Publikationsdatum:
17. Dezember 2009 (online)
Publikationsverlauf
Publikationsdatum:
17. Dezember 2009 (online)

Abstract
A stereospecific Rh(I)-catalyzed intramolecular [4+2] cycloaddition has been used to elaborate the essential carbocyclic core of (±)-ptilocaulin.
Key words
cycloaddition reactions - transition-metal catalysts - rhodium(I)
- Supporting Information for this article is available online:
- Supporting Information
- 1
Lautens M.Klute W.Tam W. Chem. Rev. 1996, 96: 49 -
2a
Wender PA.Gamber GG.Hubbard RD.Zhang L. J. Am. Chem. Soc. 2002, 124: 2876 -
2b
Wender PA.Glorius F.Husfeld CO.Langkopf E.Love JA. J. Am. Chem. Soc. 1999, 121: 5348 -
2c
Trost BM.Toste FD.Shen H. J. Am. Chem. Soc. 2000, 122: 2379 -
2d
Wender PA.Smith TE. Tetrahedron 1998, 54: 1255 -
2e
Takacs JM.Zhu J.Chandramouli S. J. Am. Chem. Soc. 1992, 114: 773 -
2f
Trost BM.Toste FD.Shen H. J. Am. Chem. Soc. 2000, 122: 2379 -
2g
Wender PA.Deschamps NM.Gamber GG. Angew. Chem. Int. Ed. 2003, 42: 1853 -
2h
Wender PA.Christy JP. J. Am. Chem. Soc. 2006, 128: 5354 -
2i
Wang W.Wang J.Su J.Huang F.Jiao L.Liang Y.Yang D.Zhang S.Wender PA.Yu Z.-X. J. Am. Chem. Soc. 2007, 129: 10060 -
2j
Yu RT.Rovis T. J. Am. Chem. Soc. 2006, 128: 2782 -
3a
Jolly RS.Luedtke G.Sheehan D.Livinghouse T. J. Am. Chem. Soc. 1990, 112: 4965 -
3b
McKinstry L.Livinghouse T. Tetrahedron 1994, 50: 6145 -
3c
O’Mahony DJR.Belanger DB.Livinghouse T. Synlett 1998, 443 -
3d
Heath H.Wolfe B.Livinghouse T.Bae SK. Synthesis 2001, 2341 -
3e
O’Mahony DJR.Belanger DB.Livinghouse T. Org. Biomol. Chem. 2003, 1: 2038 - 4
Harbour GC.Tymiak AA.Reinhart KL.Shaw PD.Hughes RG.Mizsak SA.Coats JH.Zurenco GE.Li LH.Kuentzel SL. J. Am. Chem. Soc. 1981, 103: 5604 - 5
Ruben RI.Snider BB.Hobbs FW.Confalone PN.Dusak BA. Invest. New Drugs 1989, 7: 147 -
6a
Snider BB.Faith WC. J. Am. Chem. Soc. 1984, 106: 1443 -
6b
Uyehara T.Furuta T.Kabawawa Y.Yamada J.-I.Kato T.Yamamoto Y. J. Org. Chem. 1988, 53: 3669 -
6c
Roush WR.Walts AE. J. Am. Chem. Soc. 1984, 106: 721 -
6d
Hassner A.Keshava Murthy KS. Tetrahedron Lett. 1986, 27: 1407 -
6e
Hassner A.Keshava Murthy KS. Isr. J. Chem. 1991, 31: 239 -
6f
Asaoka M.Sakurai M.Takei H. Tetrahedron Lett. 1990, 31: 4759 -
6g
Cossy J.BouzBouz S. Tetrahedron Lett. 1996, 37: 5091 -
6h
Schmalz H.-G.Schellhaas K. Angew. Chem., Int. Ed. Engl. 1996, 35: 2146 -
6i
Schellhaas K.Schmalz H.-G.Bats JW. Chem. Eur. J. 1998, 4: 57 -
6j For the syntheses of additional
members belonging to this alkaloid family, see:
Min Y.Pochapsky SS.Snider BB. J. Org. Chem. 2008, 73: 9065 -
7a
Green C.Hickinbottom WJ. J. Chem. Soc. 1957, 3270 -
7b
The authors would like to thank Ms. Elisa Sunsdahl for optimizing the large-scale preparation of 2.
- 8
Uenishi J.Kawahama R.Yonemitsu O.Tsuji J. J. Org. Chem. 1998, 63: 8965