88980-13-6Relevant articles and documents
Diastereoselective oxygen to carbon rearrangements of anomerically linked enol ethers and the total synthesis of (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl)acetic acid, a component of civet
Dixon, Darren J.,Ley, Steven V.,Tate, Edward W.
, p. 2385 - 2394 (2000)
A range of enol ethers, linked via their oxygen atom to the anomeric centre of a pyran ring system, was shown to undergo oxygen to carbon rearrangement upon treatment with a Lewis acid to give the corresponding 2-carbon substituted products. At low temperature, trimethylsilyl trifluoromethanesulfonate catalysed rearrangements of anomerically linked 6-substituted tetrahydropyranyl enol ethers gave selectively the trans-pyranyl ketones, whereas at higher temperatures selective formation of the cis-pyranyl ketones was observed. In a simple application of the methodology the cis-selective rearrangement was used as the key step in a concise total synthesis of a constituent of civet.
A Unified Synthetic Approach to Optically Pure Curvularin-Type Metabolites
Allu, Srinivasa Rao,Banne, Sreenivas,Jiang, Jia,Qi, Na,Guo, Jian,He, Yun
, p. 7227 - 7237 (2019/06/07)
A unified and concise approach to the synthesis of nine curvularin-type metabolites and two analogues has been developed with few steps and high yields. Among them, sumalactones A-D were synthesized for the first time. The key steps in this approach inclu
Total synthesis and stereochemical revision of relgro and 10′-oxorelgro
Gaddam, Janardhan,Reddy, G. Sudhakar,Marumudi, Kanakaraju,Kunwar, Ajit C.,Yadav, Jhillu S.,Mohapatra, Debendra K.
, p. 5601 - 5614 (2019/06/13)
The first asymmetric total synthesis and stereochemical assignments of 10-membered macrolactones relgro and 10′-oxorelgro are disclosed. To this end, palladium-catalyzed Stille coupling, the Mitsunobu reaction, ring-closing metathesis, EDCI promoted coupling and the Jacobsen hydrolytic kinetic resolution are used as key steps. The total synthesis followed by thorough evaluation of the optical rotation and CD spectral data led to the revision of the absolute configuration at C-6′ for both relgro and 10′-oxorelgro. Moreover, the 1H as well as 13C NMR data are reported for the first time for relgro.
