来自澳大利亚雨林的抗癌药物EBC - 23的结构与绝对立体化学

Structure and absolute stereochemistry of the anticancer agent EBC-23 from the Australian rainforest.

作者信息

Dong Lin, Gordon Victoria A, Grange Rebecca L, Johns Jenny, Parsons Peter G, Porzelle Achim, Reddell Paul, Schill Heiko, Williams Craig M

机构信息

School of Molecular and Microbial Sciences, University of Queensland, Brisbane, Queensland, Australia.

出版信息

J Am Chem Soc. 2008 Nov 19;130(46):15262-3. doi: 10.1021/ja807133p. Epub 2008 Oct 25.

DOI:10.1021/ja807133p

PMID:18950180

Abstract

EBC-23 (2), a prostate anticancer agent, was isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforest. Extensive NOE experiments enabled the relative stereochemistry of the proposed EBC-23 (2) structure to be determined. Total synthesis of both enantiopodes over nine linear steps, involving challenging RCM and spiroacetal cyclizations, confirmed the gross structure and relative and absolute stereochemistry.

摘要

EBC - 23（2）是一种前列腺抗癌剂，从澳大利亚热带雨林中的樟科植物劳氏樟的果实中分离得到。广泛的核Overhauser效应（NOE）实验确定了所提出的EBC - 23（2）结构的相对立体化学。通过九个线性步骤全合成两种对映体，其中涉及具有挑战性的关环复分解反应（RCM）和螺缩醛环化反应，证实了其总体结构以及相对和绝对立体化学。