484664-27-9Relevant articles and documents
Synthesis and absolute configuration of the 7-phenylhepta-4,6-diyne-1,2- diol isolated from Bidens pilosa
Cui, Shan,Zou, Yang,Wu, Yikang,Gao, Po
scheme or table, p. 2131 - 2135 (2011/08/04)
The title diynediol was synthesized in enantiopure (>98.4% ee) forms, with the cross coupling of phenylacetylene with either (R)- or (S)-5-benzyloxypent-1-yn-4-ol catalyzed by nickel(II) chloride-copper(I) iodide as the key step. Comparison of the spectro
Chemical variation of natural product-like scaffolds: Design and synthesis of spiroketal derivatives
Zinzalla, Giovanna,Milroy, Lech-Gustav,Ley, Steven V.
, p. 1977 - 2002 (2008/02/04)
The design and synthesis of spiroketal structures and their chemical modification, leading to a collection of new small molecules for biological evaluation as orally-bioavailable lead compounds is described. Both [6,5]- and [6,6]-membered ring spiroketal units have been prepared in a stereochemically-varying fashion starting from commercially available (R)- or (S)-glycidol, in ten, eleven and twelve linear steps, in overall yields of 45, 40 and 20%, respectively. Further elaboration according to Lipinski's guidelines has given a collection of structurally-diverse, new spiroketal derivatives in high yields and with high purity. The Royal Society of Chemistry 2006.
Synthesis of the bis-spiroacetal moiety of the shellfish toxins spirolides B and D using an iterative oxidative radical cyclization strategy
Meilert, Kai,Brimble, Margaret A.
, p. 2184 - 2192 (2008/02/05)
The enantioselective synthesis of the bis-spiroacetal fragment of the shellfish toxins, spirolides B 1 and D 2, is reported. The carbon framework was constructed via a Barbier reaction of dihydropyran 10 with aldehyde 11, followed by two oxidative radical cyclizations to construct the bis-spiroacetal ring system. A silyl-modified Prins cyclization and enantioselective crotylation successfully installed the stereocenters in the cyclization precursor 21. The initial unsaturated bis-spiroacetals 9a-d underwent equilibration during epoxidation to trans-epoxide 24 that was converted to tertiary alcohol 7. The Royal Society of Chemistry 2006.
Apoptolidinone A: Synthesis of the apoptolidin a aglycone
Schuppan, Julia,Wehlan, Hermut,Keiper, Sonja,Koert, Ulrich
, p. 7364 - 7377 (2007/10/03)
An efficient stereocontrolled synthesis of apoptolidinone A, the aglycone of apoptolidin A is described. The synthetic strategy relies on a cross coupling between C11/C12 of a northern half (C1-C11) and a southern part (C12-C28) followed by a ring-size selective macrolactonization. Key steps for the introduction of the southern half stereocenters are a stereoselective aldol reaction, a substrate controlled dihydroxylation and a chelation-controlled Grignard/aldehyde addition. The conjugated triene of the northern half was built up successively by E-selective Wittig reactions. L-Malic acid was chosen as the chiral pool source for the C8/C9 stereocenters. The final cleavage of the silyl ethers and the conversion of the C21 methyl ketal into the hemiketal was achieved by HF-pyridine.
Synthesis of the bis-spiroacetal moiety of spirolides B and D
Meilert, Kai,Brimble, Margaret A.
, p. 3497 - 3500 (2007/10/03)
(Chemical Equation Presented) An enantioselective synthesis of the bis-spiroacetal fragment of spirolides B and D is reported. The carbon framework was constructed via Barbier reaction of dihydropyran 3 with aldehyde 4, followed by a double oxidative radi
Ring-closing metathesis of allylic O,O- and N,O-acetals
Kinderman, Sape S.,Doodeman, Robin,Van Beijma, Jetze W.,Russcher, Jaap C.,Tjen, Kim C. M. F.,Kooistra, T. Martijn,Mohaselzadeh, Homayun,Van Maarseveen, Jan H.,Hiemstra, Henk,Schoemaker, Hans E.,Rutjes, Floris P. J. T.
, p. 736 - 748 (2007/10/03)
A variety of allylic O,O- and N,O-acetals were synthesized using a mild palladium-catalyzed coupling of an alcohol or sulfonamide with an alkyl or aryl 1,2-propadienyl ether. The resulting linear acetals were used for the synthesis of unsaturated rings via ring-closing metathesis, in which the acetal carbon-a precursor for oxycarbenium or N-sulfonyliminium ions, respectively-served as a reactive center for further introduction of functional groups. The products-unsaturated oxygen and nitrogen heterocyclic scaffolds - offer multiple opportunities for derivatization as illustrated with the synthesis of substituted dihydropyrans, chromenes, enantiopure tetrahydropyridines and an enantiomerically pure quinolizidine amino acid.
