Total Synthesis of Hybocarpone, a Cytotoxic Naphthazarin Derivative from the Lichen Lecanora hybocarpa, and Related Compounds-Reference-Cited by-同舟云学术

Total Synthesis of Hybocarpone, a Cytotoxic Naphthazarin Derivative from the Lichen Lecanora hybocarpa, and Related Compounds

Published:2014-12 Issue:12 Volume:9 Page:1934578X1400901
ISSN:1934-578X
Container-title:Natural Product Communications
language:en
Short-container-title:Natural Product Communications

Author:

Dragan Sergey V.¹,Pushilin Michael A.²,Glazunov Valery P.¹,Denisenko Vladimir A.¹,Anufriev Victor Ph.¹

Affiliation:

1. G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, 690022, Vladivostok, Prospect 100 let Vladivostoku, 159, Russia

2. Institute of Chemistry, Far East Branch of the Russian Academy of Sciences, 690022, Vladivostok, Prospect 100 let Vladivostoku, 159, Russia

Abstract

The concise synthesis of the lichen-derived antitumor agent hybocarpone (1) and its analogs is described. A new synthetic approach is based on the direct oxidative dimerization of the available naphthazarin precursors in the formation of the binaphtho[2,3- b; 2,3- d]furantetraone structure. It was shown that the first step to tetrahydrofuran features is the bridging hindered S*, S* and R*, S* carbon-carbon bonds of the molecules, setting the relative configurations of the 5a S*,6a S*,12a S*,12b S* and 5a S*,6a R*,12a R*,12b S* diastereomers.

Publisher

SAGE Publications

Subject

Complementary and alternative medicine,Plant Science,Drug Discovery,Pharmacology,General Medicine

Link

http://journals.sagepub.com/doi/pdf/10.1177/1934578X1400901227

Reference19 articles.

1. Hybocarpone, a novel cytotoxic naphthazarin derivative from mycobiont cultures of the lichen Lecanora hybocarpa

2. ThomsonR.H. (1971) Naturally occurring quinines. 2nd ed. Academic Press, London-New York, 734 p.

3. Quinones of Cetraria islandica

4. Aureoquinone, a New Protease Inhibitor from Aureobasidium sp.