502763-33-9Relevant academic research and scientific papers
An enantioselective biomimetic total synthesis of (-)-siccanin
Trost, Barry M.,Shen, Hong C.,Surivet, Jean-Philippe
, p. 3943 - 3947 (2003)
A convergent asymmetric synthesis of the clinically important antifungal agent (-)-siccanin (1) mimics the proposed biosynthetic pathway. A Pd-catalyzed asymmetric allylic alkylation was used to establish the stereochemistry, and sequential radical proces
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.
Preparation of (S)-γ-cyclogeraniol by lipase-catalyzed transesterification and synthesis of (+)-trixagol and (+)-luffarin-P
Fujii, Mikio,Morimoto, Yosuke,Ono, Machiko,Akita, Hiroyuki
, p. 160 - 166 (2015/12/04)
Lipase-catalyzed kinetic resolution of γ-cyclogeraniol by Candida antarctica lipase B yielded 23% of enantiomerically pure (S)-γ-cyclogeraniol. (+)-trixagol and (+)-luffarin-P were synthesized from the obtained (S)-γ-cyclogeraniol, and the absolute config
Biomimetic enantioselective total synthesis of (-)-siccanin via the Pd-catalyzed asymmetric allylic alkylation (AAA) and sequential radical cyclizations
Trost, Barry M.,Shen, Hong C.,Surivet, Jean-Philippe
, p. 12565 - 12579 (2007/10/03)
(-)-Siccanin (1), a natural product possessing significant antifungal properties, was synthesized enantioselectively via a biomimetic route. This synthetic route features two sequential radical cyclizations: a Ti(III)-mediated radical cyclization of epoxy
Synthesis of (+)-trixagol and its enantiomer, the terpenoid side chain of (-)-agelasine E
Bakkestuen, Anne Kristin,Gundersen, Lise-Lotte
, p. 115 - 121 (2007/10/03)
The naturally occurring γ-cyclogeranylgeraniol called (+)-trixagol has been synthesised for the first time. Trixagol was readily available in five steps from (S)-2,2-dimethyl-6-methylene-1-cyclohexanemethanol. The enantiomer of trixagol, which equates to
