324010-81-3Relevant academic research and scientific papers
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.
One carbon homologation of halides to benzyl ethers
Taber, Douglass F.,Paquette, Craig M.,Reddy, P. Ganapati
supporting information; experimental part, p. 2462 - 2463 (2009/08/09)
The preparation of one carbon homologated benzyl ethers from alkyl and aromatic halides is reported. The coupling reaction is rapid and efficient at room temperature.
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.
