929554-08-5Relevant academic research and scientific papers
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.
Enantioselective synthesis of (2R,13R,8Z)-2,13-diacetoxy-8-heptadecene, the major component of the sex pheromone of the pear leaf midge, Dasineura pyri
Zhou, Yun,Yang, Pengfei,Li, Shuoning,Wang, Lifeng,Yin, Jingwei,Zhong, Jiangchun,Dong, Yanhong,Liu, Shangzhong,Wang, Min,Bian, Qinghua
, p. 338 - 343 (2017/02/18)
The first enantioselective synthesis of (2R,13R,8Z)-2,13-diacetoxy-8-heptadecene 1, the major component of the sex pheromone of the pear leaf midge, Dasineura pyri, has been achieved. The key steps include the (R,R)-BINOL/Ti(OiPr)4catalyzed alkynylzinc addition to an unsaturated aldehyde, the ring-opening of the chiral epoxide with a Grignard reagent, and the partial reduction of an acetylenic diol ester to a (Z)-olefinic diol ester with hydrogen and P2-Ni.
A chemoenzymatic asymmetric synthesis of methyl (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate, a component of Mycosphaerella rubella
Sharma, Anubha,Gamre, Sunita,Chattopadhyay, Subrata
experimental part, p. 1164 - 1167 (2009/09/30)
The first asymmetric synthesis of (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate has been developed. The key steps of the synthesis were the use of an efficient lipase-catalyzed acylation, a chiral template-driven enantiocontrolled allylation for introducing the stereogenic centers, and a cross-metathesis for controlling the C-8 olefin geometry.
Stereoselective synthesis of (+)-diplodialides-B, C and a formal synthesis of (+)-diplodialide-A by ring-closing metathesis approach
Sharma,Reddy, K. Laxmi
, p. 3197 - 3202 (2007/10/03)
Stereoselective synthesis of diplodialides-B and C and the formal synthesis of diplodialide-A are reported. A combination of Jacobsen's hydrolytic kinetic resolution and Sharpless epoxidation is used for the creation of two stereogenic centers, while a ring-closing metathesis strategy was used for the construction of the lactone ring.
