Abstract
A novel and efficient methodology for the stereocontrolled synthesis of spirocyclic oxa-bridged cyclooctanoids having multiple spiro centers is described. The cycloaddition reaction, which affords spirocyclic cyclooctanoids is highly sterospecific and has been supported by theoretical calculations.
Key words
pentafulvenes - oxidopyrylium betaines - oxa-bridged spirocycles - macromolecules
References
1a
Brito I.
Cueto M.
Diaz-Marrero AR.
Parias J.
Martin AS.
J. Nat. Prod.
2002,
65:
946
1b
Conroy H.
Chakrabarti JK.
Tetrahedron
1959,
4:
6
1c
Cui CB.
Kakeya H.
Osada H.
Tetrahedron
1996,
52:
12651
1d
Cui CB.
Kakeya H.
Osada H.
J. Antibiot.
1996,
49:
832
1e
Cui CB.
Kakeya H.
Osada H.
Tetrahedron
1997,
53:
59
1f
Daly JW.
Karle I.
Myers C.
Tokuyama T.
Waters JA.
Witkop B.
Proc. Natl. Acad. Sci. U.S.A.
1971,
68:
1870
1g
Okabe KJ.
Yamada K.
Yamamura S.
Takasa SJ.
J. Chem. Soc. C
1967,
2201
1h
Sakabe N.
Takada S.
Okabe KJ.
J. Chem. Soc., Chem. Commun.
1967,
259
2a
Efange SMN.
Kamath AP.
Khare AB.
Kung M.-P.
Mach RH.
Parsons SMN.
J. Med. Chem.
1997,
40:
3905
2b
Goehring RR.
Org. Prep. Proced. Int.
1995,
27:
691
2c
Edmondson S.
Danishefsky SJ.
Sepp-Lorenzino I.
Rosen N.
J. Am. Chem. Soc.
1999,
121:
2147
3a
Alper PB.
Meyers C.
Lerchner A.
Siegel DR.
Carreira EM.
Angew. Chem. Int. Ed.
1999,
38:
3186
3b
Trost BM.
Yong B.
Miller ML.
J. Am. Chem. Soc.
1989,
111:
6482
4a
Pages L.
Llebaria A.
Camps F.
Molins E.
Miravitlles C.
Moreto JM.
J. Am. Chem. Soc.
1992,
114:
10449
4b
Oda M.
Fukuta A.
Kajioka T.
Uchiyama T.
Kainuma H.
Miyatake R.
Kuroda S.
Tetrahedron
2000,
56:
9917
5a
Anas S.
Krishnan KS.
Sajisha VS.
Anju KS.
Radhakrishnan KV.
Suresh E.
Suresh CH.
New J. Chem.
2007,
31:
237
5b
Radhakrishnan KV.
Anas S.
Suresh E.
Koga N.
Suresh CH.
Bull. Chem. Soc. Jpn.
2007,
80:
484
5c
Anas S.
Sajisha VS.
Mohanlal S.
Radhakrishnan KV.
Synlett
2006,
2399
5d
Nair V.
Jayan CN.
Radhakrishnan KV.
Anilkumar G.
Rath NP.
Tetrahedron
2001,
57:
5807
6a
Radhakrishnan KV.
Krishnan KS.
Bhadbhade MM.
Bhosekar GV.
Tetrahedron Lett.
2005,
46:
4785
6b
Krishnan KS.
Sajisha VS.
Anas S.
Suresh CH.
Bhadbhade MM.
Bhosekar GV.
Radhakrishnan KV.
Tetrahedron
2006,
62:
5952
6c
Krishnan KS.
Suresh E.
Mathew S.
Radhakrishnan KV.
Synthesis
2006,
1811
6d
Krishnan KS.
Smitha M.
Suresh E.
Radhakrishnan KV.
Tetrahedron
2006,
62:
12345
6e
Krishnan KS.
Kuthanapillil JM.
Rajan R.
Suresh E.
Radhakrishnan KV.
Eur. J. Org. Chem.
2007,
5847
6f
Krishnan KS.
Rajan R.
Radhakrishnan KV.
Synthesis
2008,
1955
7 Crystallographic data for 7a have been deposited with the Cambridge Crystallographic Data Center as supplementary publication number CCDC 644182. Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 33603 or e-mail: deposit@ccdc.cam.ac.uk).
8a
Becke AD.
J. Chem. Phys.
1993,
98:
5648
8b
Lee CT.
Yang WT.
Parr RG.
Phys. Rev. B
1988,
37:
785
8c
Suresh CH.
Ramaiah D.
George MV.
J. Org. Chem.
2007,
72:
367
8d
Varma L.
Ganga VB.
Suresh E.
Suresh CH.
Tetrahedron Lett.
2006,
47:
917
9
Frisch MJ.
Trucks GW.
Schlegel HB.
Scuseria GE.
Robb MA.
Cheeseman JR.
Montgomery JA.
Vreven T.
Kudin KN.
Burant JC.
Millam JM.
Iyengar SS.
Tomasi J.
Barone V.
Mennucci B.
Cossi M.
Scalmani G.
Rega N.
Petersson GA.
Nakatsuji H.
Hada M.
Ehara M.
Toyota K.
Fukuda R.
Hasegawa J.
Ishida M.
Nakajima T.
Honda Y.
Kitao O.
Nakai H.
Klene M.
Li X.
Knox JE.
Hratchian HP.
Cross JB.
Adamo C.
Jaramillo J.
Gomperts R.
Stratmann RE.
Yazyev O.
Austin AJ.
Cammi R.
Pomelli C.
Ochterski JW.
Ayala PY.
Morokuma K.
Voth GA.
Salvador P.
Dannenberg JJ.
Zakrzewski VG.
Dapprich S.
Daniels AD.
Strain MC.
Farkas O.
Malick DK.
Rabuck AD.
Raghavachari K.
Foresman JB.
Ortiz JV.
Cui Q.
Baboul AG.
Clifford S.
Cioslowski J.
Stefanov BB.
Liu G.
Liashenko A.
Piskorz P.
Komaromi I.
Martin RL.
Fox DJ.
Keith T.
Al-Laham MA.
Peng CY.
Nanayakkara A.
Challacombe M.
Gill PMW.
Johnson B.
Chen W.
Wong MW.
Gonzalez C.
Pople JA.
Gaussian 03, Revision C.02
Gaussian, Inc.;
Wallingford CT:
2004.
10a
Gupta S.
Das BC.
Schafmeister CE.
Org. Lett.
2005,
7:
2861
10b
Levins CG.
Brown ZZ.
Schafmeister CE.
Org. Lett.
2006,
8:
2807