title: A C2-symmetric chiral pool-based flexible strategy: synthesis of (+)- and (-)-shikimic acids, (+)- and (-)-4-epi-shikimic acids, and (+)- and (-)-pinitol.
abstract: Via combination of a novel acid-promoted rearrangement of acetal functionality with the controlled installation of the epoxide unit to create the pivotal epoxide intermediates in enantiomerically pure form, a simple, concise, flexible, and readily scalable enantiodivergent synthesis of (+)- and (-)-shikimic acids and (+)- and (-)-4-epi-shikimic acids has emerged. This simple strategy not only provides an efficient approach to shikimic acids but also can readily be adopted for the synthesis of (+)- and (-)-pinitols. These concise total syntheses exemplify the use of pivotal allylic epoxide 14 and its enantiomer ent-14. A readily available inexpensive C2-symmetric L-tartaric acid (7) served as key precursor. In general, the strategy here provides a neat example of the use of a four-carbon chiron and offers a good account of the synthesis of functionalized cyclohexane targets.
authors.affiliation: Department of Chemistry, National Chung-Hsing University , Taichung 400, Taiwan, Republic of China.
authors.forename: Bakthavachalam
authors.initials: B
authors.lastname: Ananthan
authors.forename: Wan-Chun
authors.initials: WC
authors.lastname: Chang
authors.forename: Jhe-Sain
authors.initials: JS
authors.lastname: Lin
authors.forename: Pin-Hui
authors.initials: PH
authors.lastname: Li
authors.forename: Tu-Hsin
authors.initials: TH
authors.lastname: Yan
mesh_terms: D002384:Catalysis; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D012765:Shikimic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003510:Cyclohexanes; D012765:Shikimic Acid; C021730:pinitol; C506365:Cyclohexane; D007294:Inositol