449174-20-3Relevant articles and documents
Chemoenzymatic asymmetric total synthesis of nonanolide (Z)-cytospolides D, E and their stereoisomers
Rej, Rohan Kalyan,Nanda, Samik
, p. 860 - 871 (2014/03/21)
Chemoenzymatic asymmetric total synthesis of the (Z)-isomer of the naturally occurring decanolide cytospolides D, E and six stereoisomers is reported. The main highlight of the synthetic venture involves ring-closing metathesis (RCM) reaction of a suitably functionalized ester compound, which was assembled by the Yamaguchi coupling of the required acid and alcohol fragments. The alcohol fragment was ac- cessed by two alternative chemoenzymatic processes, one being hydroxynitrile lyase mediated hydrocyanation, whereas lipase-catalyzed transesterification was the key sep in the second route. The acid fragment was constructed by an enantioselective enzymatic desymmetrization (EED) of prochiral 2-methyl-1,3-propanediol and Corey-Bakshi-Shibata (CBS) mediated stereoselective carbonyl reduction.
Chemoenzymatic Asymmetric Total Synthesis of Nonanolide (Z)-Cytospolides D, e and Their Stereoisomers
Rej, Rohan Kalyan,Nanda, Samik
, p. 860 - 871 (2015/10/05)
Chemoenzymatic asymmetric total synthesis of the (Z)-isomer of the naturally occurring decanolide cytospolides D, E and six stereoisomers is reported. The main highlight of the synthetic venture involves ring-closing metathesis (RCM) reaction of a suitably functionalized ester compound, which was assembled by the Yamaguchi coupling of the required acid and alcohol fragments. The alcohol fragment was accessed by two alternative chemoenzymatic processes, one being hydroxynitrile lyase mediated hydrocyanation, whereas lipase-catalyzed transesterification was the key sep in the second route. The acid fragment was constructed by an enantioselective enzymatic desymmetrization (EED) of prochiral 2-methyl-1,3-propanediol and Corey-Bakshi-Shibata (CBS) mediated stereoselective carbonyl reduction.
Stereocontrolled synthesis of 1,3-diols from enones: Cooperative lewis base-mediated intramolecular carbonyl hydrosilylations
Medina, Casey,Carter, Kyle P.,Miller, Michael,Clark, Timothy B.,O'Neil, Gregory W.
supporting information, p. 9093 - 9101 (2013/10/08)
A streamlined synthesis of β-hydroxy ketone substrates has been developed to further investigate a recently discovered cooperative Lewis base-mediated intramolecular carbonyl hydrosilylation reaction. The synthesis features an enone β-borylation/oxidation
Studies on the synthesis of apoptolidin A. 1. Synthesis of the C(1)-C(11) fragment
Handa, Masaki,Scheldt, Karl A.,Bossart, Martin,Zheng, Nan,Roush, William R.
, p. 1031 - 1035 (2008/09/18)
(Chemical Equation Presented) A synthesis of the C(1)-C(11) fragment of apoptolidin A has been accomplished by a convergent route involving the stereoselective glycosidation of 9 and the Suzuki cross-coupling reaction of bromodienoate 7 and the vinylboran
Total Synthesis of the Boron-Containing Ion Carrier Antibiotic Macrodiolide Tartrolon B
Mulzer, Johann,Berger, Markus
, p. 891 - 898 (2007/10/03)
The first total synthesis of the boron-containing macrodiolide antibiotic tartrolon B is reported in full detail. Two convergent approaches to the target compound are described, the first of which eventually failed, due to sensitive functionality. In the
Total synthesis and structural elucidation of (-)-delactonmycin
Correa Jr., Ivan R.,Pilli, Ronaldo A.
, p. 3017 - 3020 (2007/10/03)
The key steps in the total synthesis of delactonmycin (1) involved a Wittig olefination, a Negishi coupling, and an aldol reaction. The polyketide, which was isolated from Streptomyces sp., displays potent inhibitory activity of the nucleocytoplasmic tran
Toward the combinatorial synthesis of polyketide libraries: Asymmetric aldol reactions with α-chiral aldehydes on solid support
Paterson, Ian,Temal-Laib, Taoues
, p. 2473 - 2476 (2007/10/03)
(Matrix presented) The viability of performing stereocontrolled aldol additions with α-chiral aldehydes attached by a silyl linker to a hydroxymethylpolystyrene resin is demonstrated for boron and titanium enolates. Subsequent ketone reduction and manipul