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(17): 2884-2892
DOI: 10.1055/s-0030-1258184
DOI: 10.1055/s-0030-1258184
SPECIALTOPIC
© Georg Thieme Verlag
Stuttgart ˙ New York
Rhodium(I)-Catalyzed Hydroacylation/Cycloisomerization Cascade Reaction: Application to the Construction of the Tricyclic Core of Guanacastepenes
Further Information
Received
23 April 2010
Publication Date:
16 July 2010 (online)
Publication History
Publication Date:
16 July 2010 (online)
Abstract
We previously developed a novel rhodium(I)-catalyzed cascade reaction involving the hydroacylation of a 4,6-dienal followed by cycloisomerization of the resulting 1,3-diene with an alkene, giving carbocycles containing a bicyclo[5.3.0]decenone skeleton in a stereoselective manner. Herein, we report the construction of the C5,C7,C6-tricyclic core of guanacastepenes using this cascade reaction.
Key words
rhodium - cascade reactions - dienes - aldehydes - guanacastepenes
- 1 For a review, see:
Willis MC. Chem. Rev. 2010, 110: 725 ; and references cited therein - For reports on the construction of five-membered ring compounds via rhodium(I)-catalyzed hydroacylation, see:
-
2a
Lochow CF.Miller RG. J. Am. Chem. Soc. 1976, 98: 1281 -
2b
Larock RC.Oertle K.Potter GF. J. Am. Chem. Soc. 1980, 102: 190 -
2c
Sakai K.Ishiguro Y.Funakoshi K.Ueno K.Suemune H. Tetrahedron Lett. 1984, 25: 961 -
2d
Fairlie DP.Bosnich B. Organometallics 1988, 7: 936 - For reports on the rhodium(I)-catalyzed asymmetric intramolecular hydroacylation of pent-4-enals, see:
-
2e
James BR.Young CG. J. Chem. Soc., Chem. Commun. 1983, 1215 -
2f
James BR.Young CG. J. Organomet. Chem. 1985, 285: 321 -
2g
Taura Y.Tanaka M.Funakoshi K.Sakai K. Tetrahedron Lett. 1989, 30: 6349 -
2h
Tanaka M.Imai M.Fujio M.Sakamoto E.Takahashi M.Eto-Kato Y.Wu XM.Funakoshi K.Sakai K.Suemune H. J. Org. Chem. 2000, 65: 5806 -
2i
Tanaka M.Sakai K.Suemune H. Curr. Org. Chem. 2003, 7: 353 -
2j
Barnhart RW.Wang X.Noheda P.Bergens SH.Whelan J.Bosnich B. J. Am. Chem. Soc. 1994, 116: 1821 -
2k
Bosnich B. Acc. Chem. Res. 1998, 31: 667 -
2l
Kundu K.McCullagh JV.Morehead AT. J. Am. Chem. Soc. 2005, 127: 16042 - For other reports on rhodium(I)-catalyzed intramolecular hydroacylations of alkenals constructing cyclic compounds larger than five-membered rings, see:
-
2m
Gable KP.Benz GA. Tetrahedron Lett. 1991, 32: 3473 -
2n
Bendorf HD.Colella CM.Dixon EC.Marchetti M.Matukonis AN.Musselman JD.Tiley TA. Tetrahedron Lett. 2002, 43: 7031 -
2o
Aïssa C.Fürstner A. J. Am. Chem. Soc. 2007, 129: 14836 -
2p
Coulter MM.Dornan PK.Dong VM. J. Am. Chem. Soc. 2009, 131: 6932 -
2q
Aloise AD.Layton ME.Shair MD. J. Am. Chem. Soc. 2000, 122: 12610 -
2r
Crépin D.Dawick J.Aïssa C. Angew. Chem. Int. Ed. 2009, 49: 620 -
3a
Sato Y.Oonishi Y.Mori M. Angew. Chem. Int. Ed. 2002, 41: 1218 -
3b
Oonishi Y.Mori M.Sato Y. Synthesis 2007, 2323 -
4a
Sato Y.Oonishi Y.Mori M. Organometallics 2003, 22: 30 -
4b
Oonishi Y.Saito A.Mori M.Sato Y. Synthesis 2009, 969 - For the cycloisomerization of 1,3-dienes with alkenes, only iron-catalyzed reactions have been reported so far by Takacs, see:
-
5a
Takacs JM.Anderson LG. J. Am. Chem. Soc. 1987, 109: 2200 -
5b
Takacs JM.Anderson LG.Creswell MW.Takacs BE. Tetrahedron Lett. 1987, 28: 5627 -
5c
Takacs JM.Newsome PW.Kuehn C. Tetrahedron 1990, 46: 5507 -
5d
Takacs BE.Takacs JM. Tetrahedron Lett. 1990, 31: 2865 -
5e
Takacs JM.Myoung YC. Tetrahedron Lett. 1992, 33: 317 - Other related rhodium(I)-catalyzed cycloadditions between 1,3-dienes and tethered alkenes have been reported; for [4+2] cycloadditions, see:
-
5f
Jolly RS.Luedtke G.Sheehan D.Livinghouse T. J. Am. Chem. Soc. 1990, 112: 4965 -
5g
O’Mahony DJR.Belanger DB.Livinghouse T. Org. Biomol. Chem. 2003, 1: 2038 ; and references cited therein -
5h
Gilbertson SR.Hoge GS. Tetrahedron Lett. 1998, 39: 2075 -
5i
Gilbertson SR.Hoge GS.Genov DG. J. Org. Chem. 1998, 63: 10077 - For [2+2+1] cyclo-additions, see:
-
5j
Wender PA.Croatt MP.Deschamps NM. J. Am. Chem. Soc. 2004, 126: 5948 - For [2+2+2] cycloadditions, see:
-
5k
Wender PA.Christy JP. J. Am. Chem. Soc. 2006, 128: 5354 ; and references cited therein -
6a
Trost BM. Acc. Chem. Res. 2002, 35: 695 -
6b
Trost BM. Science 1991, 254: 1471 - For reviews on cascade reactions, see:
-
7a
Wasilke J.-C.Obrey SJ.Baker RT.Bazan GC. Chem. Rev. 2005, 105: 1001 -
7b
Poli G.Giambastiani G.Heumann A. Tetrahedron 2000, 56: 5959 -
7c
Tietze LF. Chem. Rev. 1996, 96: 115 -
7d
Denmark SE.Thorarensen A. Chem. Rev. 1996, 96: 137 -
7e
Winkler JD. Chem. Rev. 1996, 96: 167 -
7f
Malacria M. Chem. Rev. 1996, 96: 289 - 8
Oonishi Y.Taniuchi A.Mori M.Sato Y. Tetrahedron Lett. 2006, 46: 5617 -
9a
Brady SF.Singh MP.Janso JE.Clardy J. J. Am. Chem. Soc. 2000, 122: 2116 -
9b
Brady SF.Bondi SM.Clardy J. J. Am. Chem. Soc. 2001, 123: 9900 - 10
Singh MP.Janso JE.Luckman SW.Brady SF.Clardy J.Greenstein M.Maiese WM. J. Antibiot. 2000, 53: 256 - For reviews on the total syntheses of guanacastepenes and related diterpenes, see:
-
11a
Hiersemann M. Nachr. Chem. 2006, 54: 29 -
11b
Hiersemann M.Helmboldt H. Top. Curr. Chem. 2005, 243: 73 -
11c
Maifeld SV.Lee D. Synlett 2006, 1623 -
11d
Mischne M. Curr. Org. Synth. 2005, 2: 261 - For reports on the total and formal syntheses of guanacastepenes, see:
-
12a
Tan DS.Dudley GB.Danishefsky SJ. Angew. Chem. Int. Ed. 2002, 41: 2185 -
12b
Lin SN.Dudley GB.Tan DS.Danishefsky SJ. Angew. Chem. Int. Ed. 2002, 41: 2188 -
12c
Mandal M.Yun HD.Dudley GB.Lin SN.Tan DS.Danishefsky SJ. J. Org. Chem. 2005, 70: 10619 -
12d
Shi B.Hawryluk NA.Snider BB. J. Org. Chem. 2003, 68: 1030 -
12e
Boyer FD.Hanna I.Ricard L. Org. Lett. 2004, 6: 1817 -
12f
Mehta G.Pallavi K.Umarye JD. Chem. Commun. 2005, 4456 -
12g
Shipe WD.Sorensen EJ.
J. Am. Chem. Soc. 2006, 128: 7025 -
12h
Iimura S.Overman LE.Paulini R.Zakarian A. J. Am. Chem. Soc. 2006, 128: 13095 -
12i
Magnus P.Waring MJ.Ollivier C.Lynch V. Tetrahedron Lett. 2001, 42: 4947 -
12j
Magnus P.Ollivier C. Tetrahedron Lett. 2002, 43: 9605 -
12k
Nguyen TM.Lee D. Tetrahedron Lett. 2002, 43: 4033 -
12l
Nguyen TM.Seifert RJ.Mowrey DR.Lee DS. Org. Lett. 2002, 4: 3959 -
12m
Nakazaki A.Sharma U.Tius MA. Org. Lett. 2002, 4: 3363 -
12n
Du XH.Chu HFV.Kwon O. Org. Lett. 2003, 5: 1923 -
12o
Du XH.Chu HFV.Kwon OY. Tetrahedron Lett. 2004, 45: 8843 -
12p
Srikrishna A.Dethe DH. Org. Lett. 2004, 6: 165 -
12q
Chiu P.Li SL. Org. Lett. 2004, 6: 613 - For reports on synthetic studies of guanacastepenes, see:
-
13a
Dudley GB.Danishefsky SJ. Org. Lett. 2001, 3: 2399 -
13b
Dudley GB.Tan DS.Kim G.Tanski JM.Danishefsky SJ. Tetrahedron Lett. 2001, 42: 6789 -
13c
Dudley GB.Danishefsky SJ.Sukenick G. Tetrahedron Lett. 2002, 43: 560 -
13d
Mandal M.Danishefsky SJ. Tetrahedron Lett. 2004, 45: 3827 -
13e
Mandal M.Danishefsky SJ. Tetrahedron Lett. 2004, 45: 3831 -
13f
Yun HD.Meng ZY.Danishefsky SJ. Heterocycles 2005, 66: 711 -
13g
Yun HD.Danishefsky SJ. Tetrahedron Lett. 2005, 46: 3879 -
13h
Cheong PHY.Yun H.Danishefsky SJ.Houk KN. Org. Lett. 2006, 8: 1513 -
13i
Snider BB.Hawryluk NA. Org. Lett. 2001, 3: 569 -
13j
Snider BB.Shi B. Tetrahedron Lett. 2001, 42: 9123 -
13k
Boyer FD.Hanna I. Tetrahedron Lett. 2002, 43: 7469 -
13l
Boyer FD.Hanna I. J. Org. Chem. 2005, 70: 1077 -
13m
Mehta G.Umarye JD. Org. Lett. 2002, 4: 1063 -
13n
Mehta G.Umarye JD.Gagliardini V. Tetrahedron Lett. 2002, 43: 6975 -
13o
Mehta G.Umarye JD.Srinivas K. Tetrahedron Lett. 2003, 44: 4233 -
13p
Mehta G.Umarye JD. Tetrahedron Lett. 2003, 44: 7285 -
13q
Shipe WD.Sorensen EJ. Org. Lett. 2002, 4: 2063 -
13r
Brummond KM.Gao D. Org. Lett. 2003, 5: 3491 -
13s
Sarpong R.Su JT.Stoltz BM. J. Am. Chem. Soc. 2003, 125: 13624 -
13t
Li CC.Liang S.Zhang XH.Xie ZX.Chen JH.Wu YD.Yang Z. Org. Lett. 2005, 7: 3709 -
13u
Li CC.Wang CH.Liang B.Zhang XH.Deng LJ.Liang S.Chen JH.Wu YD.Yang Z. J. Org. Chem. 2006, 71: 6892 -
13v
Gradl SN.Kennedy-Smith JJ.Kim J.Trauner D. Synlett 2002, 411 -
13w
Hughes CC.Kennedy-Smith JJ.Trauner D. Org. Lett. 2003, 5: 4113 -
13x
Hughes CC.Miller AK.Trauner D. Org. Lett. 2005, 7: 3425 -
13y
McGowan CA.Schmieder AK.Roberts L.Greaney MF. Org. Biomol. Chem. 2007, 5: 1522 -
13z
Michalak K.Michalak M.Wicha J. Tetrahedron Lett. 2008, 49: 6807 ; and references cited therein - 14
Sato Y.Oonishi Y.Mori M. J. Org. Chem. 2003, 68: 9858 - 15
Zoller T.Uguen D.De Cian A.Fischer J.Sablé S. Tetrahedron Lett. 1997, 38: 3409 - 16
Bennacer B.Trubuil D.Rivalle C.Grierson DS. Eur. J. Org. Chem. 2003, 4561