56691-73-7Relevant academic research and scientific papers
A general strategy for the stereoselective synthesis of the furanosesquiterpenes structurally related to pallescensins 1-2
Serra, Stefano
, (2019/05/24)
Here, we describe a general stereoselective synthesis of the marine furanosesquiterpenes structurally related to pallescensins 1-2. The stereoisomeric forms of the pallescensin 1, pallescensin 2, and dihydropallescensin 2 were obtained in high chemical and isomeric purity, whereas isomicrocionin-3 was synthesized for the first time. The sesquiterpene framework was built up by means of the coupling of the C10 cyclogeranyl moiety with the C5 3-(methylene)furan moiety. The key steps of our synthetic procedure are the stereoselective synthesis of four cyclogeraniol isomers, their conversion into the corresponding cyclogeranylsulfonylbenzene derivatives, their alkylation with 3-(chloromethyl)furan, and the final reductive cleavage of the phenylsulfonyl functional group to afford the whole sesquiterpene framework. The enantioselective synthesis of the α-, 3,4-dehydro-γ- and γ-cyclogeraniol isomers was performed using both a lipase-mediated resolution procedure and different regioselective chemical transformations.
Synthesis, antimicrobial and antineoplastic activities for agelasine and agelasimine analogs with a β-cyclocitral derived substituent
Proszenyak, Agnes,Charnock, Colin,Hedner, Erik,Larsson, Rolf,Bohlin, Lars,Gundersen, Lise-Lotte
, p. 625 - 634 (2008/12/21)
Agelasines and agelasimines are antimicrobial and cytotoxic purine derivatives isolated from marine sponges (Agelas sp.). We have synthesized structurally simplified analogs of these natural products starting from β-cyclocitral. The novel compounds were found to be strong inhibitors of a wide variety of pathogenic microorganisms (incl. Mycobacterium tuberculosis) as well as cancer cell lines. The biological activities were generally in the same range as those previously found for the structurally more complex agelasines and agelasimines isolated in small amounts from natural sources. We also report for the first time that agelasine and agelasimine analogs inhibit growth of protozoa (Acanthamoeba castellanii and Acanthamoeba polyphaga). Acanthamoeba keratitis is an increasingly common and severe corneal infection, closely associated with contact lens wear.
New methods for the preparation of theaspiranes, megastigmane-5,7,9-trien-4-one and megastigmane-5,8-dien-4-one from γ-pyronene
Boulin,Arreguy-San Miguel,Delmond
, p. 3927 - 3932 (2007/10/03)
γ-Pyronene, a terpenic synthon easily available from myrcene, an industrial raw material, is used as an intermediate in the synthesis of theaspiranes and various megastigmane derivatives. These compounds are useful in the preparation of perfumes and aromas. (C) 2000 Elsevier Science Ltd.
