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
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.
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.
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
