103654-47-3Relevant articles and documents
Efficient two-step conversion of α,β-unsaturated aldehydes to optically active γ-oxy-α,β-unsaturated nitriles and its application to the total synthesis of (+)-patulolide C
Tian, Jun,Yamagiwa, Noriyuki,Matsunaga, Shigeki,Shibasaki, Masakatsu
, p. 3021 - 3024 (2003)
(Matrix presented) An efficient two-step conversion of α,β -unsaturated aldehydes into optically active γ-oxy-α,β -unsaturated nitriles is described. First, catalytic asymmetric cyanation-ethoxycarbonylation using (S)-YLi3tris(binaphthoxide) (Y
Stereoselective total synthesis of Patulolide C
Pratapareddy, Bommareddy,Sreenivasulu, Reddymasu,Rao, Mandava Venkata Basaveswara,Raju, Rudraraju Ramesh
, p. 2760 - 2764 (2020)
Stereoselective total synthesis of Patulolide C has been accomplished from easily available and inexpensive (S)-chiral epoxide. The key steps involved in the concise synthesis of Patulolide C utilizes ring opening of chiral epoxide, cleavage of 1,2-diol, deprotection of benzyl ether of hydroxyl acid and Yamaguchi macrolactonisation dilution conditions as key steps. The advantage of this method include inexpensive starting material, mild reaction conditions and high purity of products.
Total synthesis of patulolide C and 11-epipatulolide C
Babu, Kagita Veera,Sharma, Gangavaram V.M.
, p. 577 - 583 (2008)
The total synthesis of 12-membered macrolides, patulolide C, 11-epipatulolide C and formal synthesis of patulolide A and epipatulolide A, starting from 1,8-octane diol is reported. A combination of Jacobsen's hydrolytic kinetic resolution and Sharpless epoxidation is used for the creation of two stereogenic centres, while ring-closing metathesis strategy was used for the construction of the lactone ring.
Synthesis of (+)-patulolide c via an asymmetric hydroformylation/ macrocyclization cascade
Risi, Roberto M.,Burke, Steven D.
, p. 1180 - 1182 (2012)
A highly atom-economical total synthesis of (+)-patulolide C has been accomplished in three steps from the known (2R)-8-nonyn-2-ol in 49% overall yield and 93% de. A Rh(I)-catalyzed asymmetric hydroformylation (AHF)/ intramolecular Wittig olefination cascade was utilized to set the C4-hydroxyl stereochemistry and E-olefin geometry as well as form the macrolactone.
Asymmetric hydroformylation-initiated tandem sequences for syntheses of (+)-patulolide C, (-)-pyrenophorol, (+)-decarestrictine L, and (+)-prelog djerassi lactone
Risi, Roberto M.,Maza, Andrew M.,Burke, Steven D.
, p. 204 - 216 (2016/09/09)
Four different Rh-catalyzed asymmetric hydroformylation (AHF) tandem reactions have been developed in the context of the total syntheses of (+)-patulolide C, (-)-pyrenophorol, (+)-decarestrictine L, and (+)-Prelog-Djerassi lactone. A total synthesis of (+)-patulolide C has been accomplished in three steps utilizing a Rh(I)-catalyzed Z-selective anti-Markovnikov hydroacetoxylation of a known alkyne to give a Z-enol acetate with excellent selectivity. An AHF/intramolecular Wittig olefination cascade was utilized to set the C4-hydroxyl stereochemistry, E-olefin geometry, and form the macrolactone. In addition, both (-)-pyrenophorol and (+)-decarestrictine L have been synthesized from the enantiomeric (4R)- and (4S)-4-(tert-butyldimethylsiloxy)-1-pentyne in five and four steps, respectively. These syntheses feature Ru(II)-catalyzed Z-selective anti-Markovnikov hydroacetoxylation of terminal alkynes followed by AHF/Wittig olefination sequences to rapidly establish functionality and stereogenicity. A synthesis of (+)-Prelog-Djerassi lactone was accomplished in three isolations from the known 1-vinyl-4-methyl-2,6,7-trioxabicyclo[2.2.2]-octane ortho ester. An AHF/crotylation tandem sequence has been developed to set the C2-C4 stereochemistry. An asymmetric hydrogenation was employed to set the C6 stereochemistry, resulting in an especially efficient enantioselective synthesis from achiral starting material. In summary, these syntheses have greatly improved efficiency in terms of atom-economy, catalytic stereoselective transformations, inexpensive reagents, step-counts, and overall yield when compared with previous synthetic attempts.
An approach to aliphatic 1,8-stereocontrol: Diastereoselective syntheses of (±)-patulolide C and (±)-epipatulolide C
Hoegenauer, E. Kate,Thomas, Eric J.
, p. 6995 - 7014,20 (2012/12/12)
The tin(iv) bromide promoted reaction of 7-hydroxy-7-phenylhept-2- enyl(tributyl)stannane 11 with benzaldehyde gave a mixture of the epimeric 1,8-diphenyloct-3-ene-1,8-diols 12 and so indirect methods were developed for aliphatic 1,8-stereocontrol to comp
Enantioselective synthesis of (+)-patulolide C via proline-catalyzed sequential α-aminooxylation and Horner-Wadsworth-Emmons olefination
Sabitha, Gowravaram,Chandrashekhar,Yadagiri,Yadav
scheme or table, p. 3824 - 3826 (2010/08/19)
The enantioselective total synthesis of (+)-patulolide C isolated from Penicillium urticae has been achieved from commercially available 9-decen-1-ol. Jacobsen's kinetic resolution and sequential a-aminooxylation and Horner-Wadsworth-Emmons (HWE) olefinat
A Concise Enantiocontrolled Route to (+)-Patulolide C
Takano, Seiichi,Murakami, Taku,Samizu, Kiyohiro,Ogasawara, Kunio
, p. 67 - 72 (2007/10/02)
A naturally occurring antifungal macrolide (+)-patulolide C has been synthesized enantioselectively via the C2-symmetric bis-epoxide by incorporation of two molecular units of (R)-O-benzylglycidol.
Total synthesis of patulolide C and its homo, nor, and iso analogs
Leemhuis,Thijs,Zwanenburg
, p. 7170 - 7179 (2007/10/02)
The stereospecific total synthesis of the naturally occurring macrolide patulolide C 19Eb as well as its iso, nor, and homo analogs is described by applying the photoinduced rearrangement of enantiomerically pure epoxy diazomethyl ketones 14 to γ-hydroxy α,β-unsaturated esters 15 as the key step. The required epoxy diazomethyl ketones 14 are obtained by a Sharpless epoxidation of an appropriate allylic alcohol, followed by ruthenium tetraoxide oxidation to an oxiranecarboxylic acid, conversion into amixed anhydride, and treatment with diazomethane. Macrolide 19Zb, which is a geometrical isomer of 19Eb, turned out to be a diastereomer of natural macrolide isopatulolide C, which implies the 4R,11R configuration for this natural material. X-ray diffraction analyses of 19Ea and 19Eb show that there is a considerable difference in spatial arrangement; particularly, the different torsion angles between the carbonyl and olefinic bonds are noteworthy. The conformational behavior of these macrolides is also deduced from the NMR and UV spectra.
