134834-34-7Relevant academic research and scientific papers
Late-stage β-epimerization. A stereodivergent to stereoconvergent relay to the first total synthesis of (+)-murolic acid
Fernandes, Rodney A.,Patil, Pradnya H.,Chowdhury, Asim K.
, p. 237 - 243 (2014/01/06)
The first total synthesis of (+)-murolic acid is accomplished in 17 steps from ester 9 in 14.8 % overall yield. The key steps involve asymmetric dihydroxylation, orthoester Johnson-Claisen rearrangement and α-methylenation using Stiles reagent. A beneficial late stage β-epimerization reverted a stereodivergent relay to a stereoconvergent completion of an efficient synthesis of (+)-murolic acid. The first total synthesis of (+)-murolic acid is accomplished in 17 steps from ester 9 in 14.8 % overall yield. The key steps involve asymmetric dihydroxylation, orthoester Johnson-Claisen rearrangement and α-methylenation using Stiles reagent. A beneficial late-stage β-epimerization increased the efficiency of the synthesis. Copyright
Total synthesis of (+)-aspicilin from D-mannitol
Yadav,Rao, T. Srinivasa,Ravindar,Reddy, B. V. Subba
scheme or table, p. 2828 - 2830 (2010/03/03)
The total synthesis of the 18-membered lichen macrolide, (+)-aspicilin, has been accomplished utilizing the Swern oxidation, Masamune-Roush olefination, and ring-closing metathesis of a trienic ester as key steps. d-Mannitol has been utilized as the chiral pool material for the construction of the olefinic aldehyde and the Jacobsen hydrolytic kinetic resolution has been employed for the construction of the olefinic phosphonate ester.
Synthesis of all the six components of the female-produced contact sex pheromone of the German cockroach, Blattella germanica (L.)
Mori, Kenji
, p. 4060 - 4071 (2008/09/20)
All of the following six components of the female sex pheromone of the German cockroach, Blattella germanica (L.) were synthesized: (3S,11S)-3,11-dimethyl-2-nonacosanone (1), its 29-hydroxy derivative 2, its 29-oxo derivative 3, (3S,11S)-3,11-dimethyl-2-heptacosanone (4), its 27-hydroxy derivative 5, and its 27-oxo derivative 6. Both the enantiomers of citronellal were employed as the chiral sources and Wacker oxidation was employed for the introduction of the carbonyl group at C-2.
Synthesis and biological evaluation of analogs of altohyrtin C (spongistatin 2)
Wagner, Carl E.,Wang, Qiang,Melamed, Alexander,Fairchild, Craig R.,Wild, Robert,Heathcock, Clayton H.
, p. 124 - 136 (2008/03/27)
Several structural analogs that contain only part of the altohyrtin structure have been prepared and compared with synthetic altohyrtin C (2) for in vitro cytotoxicity against human colon (HCT116) and ovarian (A2780) cell lines. Whereas altohyrtin C was f
Enzyme-mediated preparation of optically active 1,2-diols bearing a long chain: Enantioselective hydrolysis of cyclic carbonates
Shimojo, Megumi,Matsumoto, Kazutsugu,Hatanaka, Minoru
, p. 9281 - 9288 (2007/10/03)
A new entry for the efficient preparation of optically active 1,2-diols having a long aliphatic chain via an enzymatic reaction is disclosed. PPL catalyzes the hydrolysis of a racemic five-membered cyclic carbonate, 4-(%benzyloxy)heptyl-1,3-dioxolan-2-one (2a), with high enantioselectivity to produce the optically active (R)-2a and (S)-9-benzyloxynonane-1,2-diol (3a) in excellent yields. The reaction is applicable to the substrates with a longer chain (10-benzyloxydecyl (3b) and 13-benzyloxytridecyl group (3c)). Optically pure (S)-(+)-8hydroxyhexadecanoic acid (1), a biologically active natural compound with a chiral long aliphatic part, is effectively synthesized starting from (R)-3-(7-benzyloxy)heptyl-2-oxirane (9), which is converted from both enantiomers of 3a. (C) 2000 Elsevier Science Ltd.
Novel recyclable aminoalcohol salts in catalytic asymmetric inductions. The addition of diethylzinc to aromatic aldehydes
Hailes, Helen C.,Madden, James
, p. 105 - 107 (2007/10/03)
Novel recyclable benzyloxyalkyl norephedrine salts have been used as efficient catalysts for the addition of diethylzinc to aromatic aldehydes to give the corresponding secondary alcohols in up to 82% ee.
Synthesis of the Cyclostellettamines A-F and Related Bis(3-alkylpyridinium) Macrocycles
Wanner, Martin J.,Koomen, Gerrit-Jan
, p. 889 - 895 (2007/10/03)
A general method was developed for the synthesis of a variety of symmetric and asymmetric macrocyclic bispyridines. 3-Hydroxyalkylpyridines 18-20 were prepared, converted to the corresponding iodides and protected on the pyridine nitrogen with a p-methoxy
Total synthesis of cyclostellettamine C, a bispyridinium macrocyclic alkaloid having muscarinic acetylcholine receptor antagonistic activity
Anan, Hideki,Seki, Norio,Noshiro, Osamu,Honda, Kazuo,Yasumuro, Kenichi,Ozasa, Teruaki,Fusetani, Nobuhiro
, p. 10849 - 10860 (2007/10/03)
Cyclostellettamine C (1), a bispyridinium macrocyclic compound having muscarinic acetylcholine receptor antagonistic activity, was synthesized by the stepwise ring closure method via 3-(13-hydroxytridecyl)-1-[13-(3-pyridyl)tridecyl]pyridinium trifluoromethanesulfonate (21). Through this study, the structure of naturally originating 1 was synthetically and biologically confirmed.
New Polymer Bound Chiral Catalyst with Methylene Spacer for the Enantioselective Addition of Diethylzinc to Aldehydes
Soai, Kenso,Watanabe, Masami
, p. 97 - 100 (2007/10/02)
Optically active sec-alcohols in good to high e.e.'s were obtained from the enantioselective addition of diethylzinc to both aliphatic and aromatic aldehydes using a polymer attached chiral catalyst with a methylene spacer.
