Sign in to use this feature.

Years

Between: -

Subjects

remove_circle_outline
remove_circle_outline

Journals

Article Types

Countries / Regions

Search Results (2)

Search Parameters:
Keywords = schenck ene reaction

Order results
Result details
Results per page
Select all
Export citation of selected articles as:
12 pages, 1554 KB  
Article
Total Synthesis of Lineaflavones A, C, D, and Analogues
by Rui Wang, Yu Fu, Ran Ma, Hongzhen Jin and Wei Zhao
Molecules 2023, 28(5), 2373; https://doi.org/10.3390/molecules28052373 - 4 Mar 2023
Cited by 1 | Viewed by 3243
Abstract
The first total synthesis of lineaflavones A, C, D, and their analogues has been accomplished. The key synthetic steps include aldol/oxa-Michael/dehydration sequence reactions to assemble the tricyclic core, Claisen rearrangement and Schenck ene reaction to construct the key intermediate, and selective substitution or [...] Read more.
The first total synthesis of lineaflavones A, C, D, and their analogues has been accomplished. The key synthetic steps include aldol/oxa-Michael/dehydration sequence reactions to assemble the tricyclic core, Claisen rearrangement and Schenck ene reaction to construct the key intermediate, and selective substitution or elimination of tertiary allylic alcohol to obtain natural compounds. In addition, we also explored five new routes to synthesize fifty-three natural product analogues, which can contribute to a systematic structure–activity relationship during biological evaluation. Full article
(This article belongs to the Special Issue Chemical Synthesis of Natural Products)
Show Figures

Graphical abstract

11 pages, 2112 KB  
Article
One-Pot Synthesis of (+)-Nootkatone via Dark Singlet Oxygenation of Valencene: The Triple Role of the Amphiphilic Molybdate Catalyst
by Bing Hong, Raphaël Lebeuf, Stéphanie Delbaere, Paul L. Alsters and Véronique Nardello-Rataj
Catalysts 2016, 6(12), 184; https://doi.org/10.3390/catal6120184 - 26 Nov 2016
Cited by 14 | Viewed by 9392
Abstract
Efficient one-pot catalytic synthesis of (+)-nootkatone was performed from (+)-valencene using only hydrogen peroxide and amphiphilic molybdate ions. The process required no solvent and proceeded in three cascade reactions: (i) singlet oxygenation of valencene according to the ene reaction; (ii) Schenck rearrangement of [...] Read more.
Efficient one-pot catalytic synthesis of (+)-nootkatone was performed from (+)-valencene using only hydrogen peroxide and amphiphilic molybdate ions. The process required no solvent and proceeded in three cascade reactions: (i) singlet oxygenation of valencene according to the ene reaction; (ii) Schenck rearrangement of one hydroperoxide into the secondary β-hydroperoxide; and (iii) dehydration of the hydroperoxide into the desired (+)-nootkatone. The solvent effect on the hydroperoxide rearrangement is herein discussed. The amphiphilic dimethyldioctyl ammonium molybdate, which is also a balanced surfactant, played a triple role in this process, as molybdate ions catalyzed at both Step 1 and Step 3 and it allowed the rapid formation of a three-phase microemulsion system that highly facilitates product recovery. Preparative synthesis of the high added value (+)-nootkatone was thus performed at room temperature with an isolated yield of 46.5%. This is also the first example of a conversion of allylic hydroperoxides into ketones catalyzed by molybdate ions. Full article
Show Figures

Graphical abstract

Back to TopTop