61448-27-9Relevant academic research and scientific papers
Stereoselective synthesis of (R)-(?) and (S)-(+)-phoracantholide I from (R)-(+)-γ-valerolactone
Datrika, Rajender,Kallam, Srinivasa Reddy,Khobare, Sandip R.,Gajare, Vikas S.,Kommi, Muralikrishna,Rama Mohan,Siddaiah, Vidavalur,Pratap
, p. 603 - 607 (2016)
A concise total synthesis of (R)-(?)-phoracantholide I 1 and (S)-(+)-phoracantholide I 2 has been developed from (R)-(+)-γ-valerolactone 6. The key steps in the synthesis of these macrolides involved enzymatic reduction of Levulinic ester 4 by asymmetric dehydrogenase, Z-selective Wittig reaction of (4-carboxybutyl)triphenylphosphonium ylide 11 with lactol 7, and cyclization of seco-acid 8 using either a Yamaguchi lactonization protocol or a Mitsunobu protocol to afford (R)-(?)-phoracantholide I and (S)-(+)-phoracantholide I respectively.
A NEW FUNGAL MORPHOGENIC SUBSTANCE, PYRENOLIDE A FROM PYRENOPHORA TERES
Nukina, Manabu,Sassa, Takeshi,Ikeda, Michimasa
, p. 301 - 302 (1980)
A new ten-menbered lactone, pyrenolide A, was identified as a new fungal morphogenic substance and its structure including absolute stereochemistry was elucidated.
Removable Silyl Group as a "masked Proton" in Oxy-2-oxonia(azonia)-Cope Rearrangement: Applications in Stereoselective Total Synthesis of Natural Macrolides
Mu, Wenbo,Zou, Yue,Zhou, Lijun,Wang, Quanrui,Goeke, Andreas
, p. 4982 - 4989 (2015/08/03)
In the presence of a Lewis acid, trimethylsilyl-substituted β,γ-unsaturated ketones and aldehydes (imines) undergo nucleophilic addition to produce zwitterionic intermediates, followed by oxy-2-oxonia(azonia)-Cope rearrangements to give homoallylic esters (amides). In the case of TMS-containing 2-vinylcycloalkanones, the process results in ring-enlargement, providing 10- to 16-membered lactones. This protocol was applied to the total synthesis of (R)-phoracantholide I.
Volatile amphibian pheromones: Macrolides from mantellid frogs from madagascar
Poth, Dennis,Wollenberg, Katharina C.,Vences, Miguel,Schulz, Stefan
supporting information; experimental part, p. 2187 - 2190 (2012/04/10)
Amphibians like water, but do they also notice volatile compounds in the air? Yes, they do. Macrolides, such as phoracantholide-J (see picture; upper right structure) or the newly discovered natural product gephyromantolide-A (left structure), are used for communication by mantelline frogs from Madagascar. Copyright
Lipase-mediated enantioselective acylation of alcohols with functionalized vinyl esters: acyl donor tolerance and applications
Chenevert, Robert,Pelchat, Nicholas,Morin, Pierre
experimental part, p. 1191 - 1196 (2009/09/27)
Enzymatic acylation is commonly used for the kinetic resolution of alcohols and amines. The simple acyl group introduced during the enzymatic reaction is usually removed or replaced by another group. Retention of more complex acyl moieties as part of the target structures would be a more efficient strategy. We have studied the enantioselective acylation of a model alcohol substrate, 1-phenylethanol, with vinyl esters bearing various functionality on the acyl moieties in the presence of three lipases (Candida antarctica, Candida rugosa and Burkholderia cepacia) frequently used in organic synthesis. C. antarctica lipase is the most versatile lipase for this type of biotransformations. We applied this strategy to the synthesis of a protein kinase C ligand and a natural product, phoracantholide.
Catalytic enantioselective synthesis of macrolides via asymmetric alkylation
Jones, Graham B.,Huber, Robert S.,Chapman, Brant J.
, p. 1797 - 1809 (2007/10/03)
Catalytic enantioselective syntheses of the macrolides (R)-(-) phoracantholide and (R)-(+) lasiodiplodin have been achieved. Stereochemistry was introduced in using an arene chromium tricarbonyl derived catalyst, which mediated the enantioselective additi
Nature-like odorants by stereoselective ring enlargement of cyclohexanone and cyclododecanone
Bollbuck, Birgit,Kraft, Philip,Tochtermann, Werner
, p. 4581 - 4592 (2007/10/03)
Both enantiomers of muscolide (3a/b), (R)-(-)-phoracantholide I [(R)-3c] and the homologous (9R)-(-)-9-tetradecanolide [(R)-3d) were synthesized by ring enlargement of cyclohexanone (6c) and cyclododecanone (6a). The ring-enlargement sequence was improved by oxidation of 9/10 with ruthenium tetroxide and reduction of 8 using catecholborane.
A Convenient Enantioselective Synthesis of (R)-(-)-Phoracantholide I, a Component of the Defensive Secretion of the Eucalypt Longicorn Phoracantha synonyma
Enders, Dieter,Plant, Andrew,Drechsel, Karin,Prokopenko, Oleg F.
, p. 1127 - 1128 (2007/10/02)
A short enantioselective synthesis of phoracantholide I (ee = 91percent), a component of the defensive secretion of the eucalypt longicorn Phoracantha synonyma, is described.Key steps of the synthesis are the enantioselective α-alkylation of cyclononanone SAMP hydrazone (de > 93percent) and subsequent Baeyer-Villiger reaction of the ketone (R)-3 with retention of configuration. - Key Words: Phoracantholide I, enantioselective synthesis / SAMP hydrazone / Baeyer-Villiger reaction / Defensive secretion, component of
Insect pheromone synthesis using Mn-salen catalyzed asymmetric epoxidation as a key step
Hamada,Daikai,Irie,Katsuki
, p. 2441 - 2451 (2007/10/03)
Enantioselective synthesis of three insect pheromones, (5Z, 13S)-5-tetradecen-13-olide, (9R)-decan-9-olide, and (S)-2-acetoxytridecane, has been achieved by using Mn-salen catalyzed asymmetric epoxidation as a key step.
Catalytic enantioselective macrolide synthesis II: Use of differential deprotection protocols
Jones,Chapman,Huber,Beaty
, p. 1199 - 1202 (2007/10/02)
Catalytic enantioselective synthesis of Phorcantholide I has been achieved. Key stereochemistry was introduced using a chiral arene chromium tricarbonyl based catalyst to mediate the addition of dimethyl zinc to a functionalised aldehyde. During the synth
