96856-97-2Relevant academic research and scientific papers
Stereoselective substrate-controlled asymmetric syntheses of both 2,5-cis- and 2,5-trans-tetrahydrofuranoid oxylipids: Stereodivergent intramolecular amide enolate alkylation
Jang, Hongjun,Shin, Iljin,Lee, Dongjoo,Kim, Hyoungsu,Kim, Deukjoon
, p. 6497 - 6501 (2016)
The concise, highly stereoselective, substrate-controlled asymmetric total syntheses of both 2,5-cis- and 2,5-trans-tetrahydrofuranoid nematocidal oxylipids from the Australian brown algae Notheia anomala have been accomplished in a stereodivergent fashion. The highly stereoselective intramolecular amide enolate alkylation strategy provides access to both stereoisomers of the 3-hydroxy-2,5-disubstituted tetrahydrofuran core of these marine natural products through chelate and nonchelate control, which is driven by the C3-hydroxy protecting group. This approach offers an optional and highly stereoelective access to any of the eight possible stereoisomers of the 2,5-disubstituted-3-oxygenated tetrahydrofuran skeleton, an important structural feature which is present in many biologically active natural products. Two from one: The title reaction leads to both isomers of the tetrahydrofuranoid nematocidal oxylipids in a stereodivergent fashion from a common intermediate. Each of the stereoisomers results from exploiting either chelate or nonchelate control in the reaction. PMB=para-methoxybenzyl, TIPS=triisopropylsilyl.
SYNTHESIS OF (2S,3S)-2.3-OCTANEDIOL AND (S)-2-HYDROXY-3-OCTANONE, THE MALE SEX PHEROMONE OF THE GRAPE BORER XYLOTRECHUS PYRRHODERUS
Mori, Kenji,Otsuka, Tatsuya
, p. 553 - 556 (2007/10/02)
(2S,3S)-2,3-Octanediol and (S)-2-hydroxy-3-octanone, the pheromone of the grape borer, were synthesized from (+/-)-1-octen-3-ol employing the Sharpless asymmetric epoxidation as the starting step.
