88223-83-0Relevant academic research and scientific papers
An approach to lauroxanes by iterative use of Co2(CO) 6-acetylenic complexes. A formal synthesis of (+)-laurencin
Ortega, Nuria,Martin, Victor S.,Martin, Tomas
scheme or table, p. 6660 - 6672 (2010/12/19)
A new approach to lauroxanes by a powerful and highly convergent methodology based on iterative use of Co2(CO)6-acetylenic complexes is described. The strategy employs an intermolecular Nicholas reaction to form unsaturated branched linear ethers, a ring closing metathesis to obtain the cobalt complex cyclic ethers, and an isomerization promoted by montmorillonite K-10. A short synthesis of cyclic ethers of seven-, eight-, and nine-membered rings is described. Additionally, the methodology is exemplified by the formal synthesis of (+)-laurencin, a red algae metabolite.
Ring closing metathesis for the formation of medium ring ethers: The total synthesis of (-)-isolaurallene
Crimmins, Michael T,Emmitte, Kyle A,Choy, Allison L
, p. 1817 - 1834 (2007/10/03)
The total synthesis of the marine metabolite (-)-isolaurallene is described. Two approaches to the core nine-membered ether are presented both of which are based on a ring closing metathesis to close the cyclic ether.
Total synthesis of (+)-laurencin: an asymmetric alkylation-ring-closing metathesis approach to medium ring ethers.
Crimmins,Emmitte
, p. 2029 - 2032 (2008/02/11)
[formula: see text] The enantioselective total synthesis of (+)-laurencin 1 is achieved in 18 steps from (S)-(+)-4-benzyl-3-benzyloxyacetyl-2-oxazolidinone. The key steps in this synthesis are an asymmetric glycolate alkylation leading to acyl oxazolidinone 2 and a subsequent ring-closing olefin metathesis to construct the oxocene core of 1. The approach to medium ring ethers utilized in this synthesis provides a general and efficient route to the cyclic core of other marine natural products.
Enantio- and Diastereocontrolled Synthesis of Chiral 1,2-Diol Derivatives from (R)-2,3-Di-O-isopropylideneglyceraldehyde: endo- and exo-Brevicomin
Mulzer, Johann,Angermann, Alfred,Muench, Winfried
, p. 825 - 838 (2007/10/02)
All four possible stereoisomers of the insect pheromone brevicomin have been prepared from (R)-2,3-di-O-isopropylideneglyceraldehyde (1) on stereocontrolled routes with ee more than 98-99percent.
CARBOHYDRATE-LIKE CHIRAL SYNTHONS. PREPARATION OF (R) γ-HEXENOLIDE, (5R,6S,7S) 6,7-ISOPROPYLIDENDIOXY-δ-OCTANOLIDE AND (+)-EXOBREVICOMIN FROM (2S,3S,4R) 2,3-ISOPROPYLIDENDIOXY-4-BENZYLOXYHEPT-6-ENE
Fuganti, Claudio,Grasselli, Piero,Pedrocchi-Fantoni, Giuseppe,Servi, Stefano,Zirotti, Carlo
, p. 3753 - 3756 (2007/10/02)
The C6, C7, C8 and C9 chiral products (8), (7), (14) and (19), containing one, two and three oxygen-substituted chiral centres, respectively, have been prepared from the carbohydrate-like optically active, Csub
