作者:Vitor F Ferreira、Aeri Park、Francis J Schmitz、Fred A Valeriote
DOI:10.1016/s0040-4020(02)01591-0
日期:2003.2
Synthesis of the cytotoxic isoquinoline quinone perfragilin A, an improved synthesis of perfragilin B and preparation of some analogues of both these compounds are described. Cytotoxicity evaluation of a number of the products is reported. The regioselectivity in Diels–Alder reactions of differently substituted benzoquinones with 2-aza-1,3-bis(t-butyldimethylsilyloxy)-1,3-butadiene is described.
The title 2-aza-1,3-diene reacted smoothly with C60 at room temperature to give 2-piperidonefused C60 after hydrolysis A silyoxy group on the piperidone ring was replaced by alkoxygroups by acid-catalyzed substitution reaction with alcohols via an iminium cation intermediate. This type of reaction was applied to reduction by use of triethylsilane to give the parent δ-valerolactam derivative of C60
Synthesis of perfragilin B, A cytotoxic isoquinoline quinone isolated from the bryozoan Membranipora perfragilis
作者:Aeri Park、Francis J. Schmitz
DOI:10.1016/s0040-4039(00)60595-6
日期:1993.6
The cytotoxic isoquinoline quinone perfragilin B (2), which was isolated from the bryozoan Membranipora perfragilis, has been synthesized. The key step involves a Diels-Alder reaction between a substituted 2-azabutadiene (4) and 2,3-bis(thiomethyl)-1,4-benzoquinone (6) to produce the isoquinoline skeleton.
Total synthesis of amphimedine
作者:Antonio M. Echavarren、J. K. Stille
DOI:10.1021/ja00220a062
日期:1988.6
Bouammali, B.; Pautet, F.; Fillion, H., Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 4, p. 337 - 338