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-00000084.xml
Synthesis 2006(6): 1005-1008
DOI: 10.1055/s-2006-926354
DOI: 10.1055/s-2006-926354
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Natural Cytotoxic Camphorataimides B and C [1]
Weitere Informationen
Received
23 September 2005
Publikationsdatum:
27. Februar 2006 (online)
Publikationsverlauf
Publikationsdatum:
27. Februar 2006 (online)

Abstract
Recently isolated camphorataanhydride A and cytotoxic camphorataimides B and C have been synthesized using chemoselective SN2′ Grignard coupling reaction of p-methoxyphenylmagnesium bromide with dimethyl bromomethylfumarate and chemoselective allylic substitution of bromide in bromoanhydride 9 with 2-propylmagnesium bromide as the key reactions. The present approach is general in nature and can be easily used to design the congeners of camphorataanhydrides/imides for structure-activity relationship studies.
Key words
dimethyl bromomethylfumarate - SN2′ Grignard coupling reaction - functionalized maleic anhydrides - bioactive natural product synthesis - camphorataimides B and C
NCL Communication No. 6688.
- 2
Nakamura N.Hirakawa A.Gao J.-J.Kakuda H.Shiro M.Komatsu Y.Sheu C.-C.Hattori M. J. Nat. Prod. 2004, 67: 46 - 3
Aqueveque P.Anke T.Sterner O. Z. Naturforsch. 2002, 57c: 257 - 4
Selles P. Org. Lett. 2005, 7: 605 - 5
Ratemi ES.Dolence JM.Poulter CD.Vederas JC. J. Org. Chem. 1996, 61: 6296 - 6
Adlington RM.Baldwin JE.Cox RJ.Pritchard GJ. Synlett 2002, 820 ; and references cited therein - For our contributions towards cyclic anhydrides to bioactive natural and unnatural products, see:
-
7a
Mhaske SB.Argade NP. J. Org. Chem. 2001, 66: 9038 -
7b
Kar A.Argade NP. J. Org. Chem. 2002, 67: 7131 -
7c
Kar A.Argade NP. Tetrahedron 2003, 59: 2991 -
7d
Kar A.Gogoi S.Argade NP. Tetrahedron 2005, 61: 5297 -
7e
Argade NP.Balasubramaniyan V. Heterocycles 2000, 53: 475 ; and references 7a-e cited therein
References
NCL Communication No. 6688.