Synthesis of Natural Cytotoxic Camphorataimides B and C [1]

Abstract

Recently isolated camphorataanhydride A and cytotoxic camphorataimides B and C have been synthesized using chemo­selective S_N2′ 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.

dimethyl bromomethylfumarate - S_N2′ Grignard coupling reaction - functionalized maleic anhydrides - bioactive natural product synthesis - camphorataimides B and C

References

<A NAME="RZ17505SS-1">1</A>

NCL Communication No. 6688.

<A NAME="RZ17505SS-2">2</A> Nakamura N. Hirakawa A. Gao J.-J. Kakuda H. Shiro M. Komatsu Y. Sheu C.-C. Hattori M. J. Nat. Prod.  2004,  67:  46 

<A NAME="RZ17505SS-3">3</A> Aqueveque P. Anke T. Sterner O. Z. Naturforsch.  2002,  57c:  257 

<A NAME="RZ17505SS-4">4</A> Selles P. Org. Lett.  2005,  7:  605 

<A NAME="RZ17505SS-5">5</A> Ratemi ES. Dolence JM. Poulter CD. Vederas JC. J. Org. Chem.  1996,  61:  6296 

<A NAME="RZ17505SS-6">6</A> 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:

<A NAME="RZ17505SS-7A">7a</A> Mhaske SB. Argade NP. J. Org. Chem.  2001,  66:  9038 

<A NAME="RZ17505SS-7B">7b</A> Kar A. Argade NP. J. Org. Chem.  2002,  67:  7131 

<A NAME="RZ17505SS-7C">7c</A> Kar A. Argade NP. Tetrahedron  2003,  59:  2991 

<A NAME="RZ17505SS-7D">7d</A> Kar A. Gogoi S. Argade NP. Tetrahedron  2005,  61:  5297 

<A NAME="RZ17505SS-7E">7e</A> Argade NP. Balasubramaniyan V. Heterocycles  2000,  53:  475 ; and references 7a-e cited therein