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Synthesis 2003(1): 0041-0044
DOI: 10.1055/s-2003-36247
DOI: 10.1055/s-2003-36247
PAPER
© Georg Thieme Verlag Stuttgart · New York
A General Approach from Eudesmane to Isodaucane Sesquiterpenes: Synthesis of 7-Epi-14-isocyano-isodauc-5-ene from α-(-)-Santonin
Further Information
Received
28 August 2002
Publication Date:
18 December 2002 (online)
Publication History
Publication Date:
18 December 2002 (online)
Abstract
A general and efficient approach for synthesis of an isodaucane sesquiterpenes has been developed by use of a novel and key rearrangement of a eudesmane enol ester epoxide. As an example, the 7-epi-14-isocyano-isodauc-5-ene has been successfully synthesized by a series of transformations from α-(-)-santonin.
Key words
isodaucane - eudesmane - terpenoids - rearrangements - epoxides - natural products
- 1 For a review on isodaucane, see:
Ghisalberti EL. Phytochemistry 1994, 37: 597 - 2
Mayol L.Piccialli V.Sica D. Tetrahedron 1987, 43: 5381 -
3a
Nishizawa M.Inoue A.Hayashi Y.Satrapradja S.Kosela S.Iwashita T. J. Org. Chem. 1984, 49: 3660 -
3b
Tchuendem MHK.Mbah JA.Tsopmo A.Ayafor JF.Sterner O.Okunjic CC.Iwu MM.Schuster BM. Phytochemistry 1999, 52: 1095 -
4a
Mehta G.Krishnamurthy N.Karra SR. J. Am. Chem. Soc. 1991, 113: 5765 -
4b
Hanssen T.Wickberg B. J. Org. Chem. 1992, 57: 5370 -
4c
Harmata M.Carter KW. Tetrahedron Lett. 1997, 38: 7985 -
4d
Wender PA.Zhang L. Org. Lett. 2000, 2: 2323 -
5a
Xia WJ.Li DR.Shi L.Tu YQ. Tetrahedron: Asymmetry 2001, 12: 1459 -
5b
Tu YQ.Sun LD. Tetrahedron Lett. 1998, 39: 7935 - 6 For a review on the synthesis starting
from α-(-)-santonin, see:
Banerjee AK.Vera WJ.Gonzalez NC. Tetrahedron 1993, 49: 4761 - 7
Shishido K.Goto K.Miyoshi Y.Takaishi Y.Shibuya M. J. Org. Chem. 1994, 59: 406 - 8
Piers E.Cheng KF. Can. J. Chem. 1968, 46: 377 - 9
Roth BD.Roark WH. Tetrahedron Lett. 1988, 29: 1255 - 10
Yang ZC.Zhou WS. J. Chem. Soc., Chem. Commun. 1995, 743 - 11
Corey EJ.Kang M.-C.Desai MC.Ghosh AK.Houpis IN. J. Am. Chem. Soc. 1988, 110: 649 - 12
Rapoport H.Bonner RM. J. Am. Chem. Soc. 1951, 73: 2872 - 13
Nicolaou KC.Veale CA.Webber SE.Katerinopoulos H. J. Am. Chem. Soc. 1985, 107: 7515 - 14
Bell HM.Vanderslice CW.Spehar A. J. Org. Chem. 1969, 34: 3923 - 15
Fujimoto Y.Ikekawa N. Chem. Pharm. Bull. 1976, 24: 825 - 16
Umbreit MA.Sharpless KB. J. Am. Chem. Soc. 1977, 99: 5526 - 17
Luche J.-P. J. Am. Chem. Soc. 1978, 100: 2226 - 18
Olah GA.Narang SC.Balaram Gupta BG.Malhotra R. J. Org. Chem. 1979, 44: 1247 - 19
Boullanger P.Descotes G. Tetrahedron Lett. 1976, 3427