Angewandte Chemie International Edition

Synthesis of the tetracyclic core of the tetrapetalones through transannular oxidative [4+ 3] cyclization

X Wang, JA Porco

Index: Wang, Xiang; Porco Jr., John A. Angewandte Chemie - International Edition, 2005 , vol. 44, # 20 p. 3067 - 3071

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Citation Number: 29

Abstract

A series of novel soybean lipoxygenase (SBL) inhibitors, tetrapetalones A–D (1–4, Scheme 1), were recently isolated by Komoda et al.[1] from the culture filtrate of the Streptomyces sp. strain USF-4727.[2] These tetrapetalones showed moderate inhibition of SBL (IC50= 190– 360 μm for 1–4) comparable to the well-known lipoxygenase inhibitors nordihydroguaiaretic acid (NDGA, IC50= 290 μm) and kojic acid (IC50= 110 μm). The structure of tetrapetalone ...