Enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block.
نویسندگان
چکیده
A brief, enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block is presented. This scaffold allows access to the cis-1,3-cyclopentanediol fragments found in a variety of biologically active natural and non-natural products. This rapid and efficient synthesis is highlighted by the utilization of the palladium-catalyzed enantioselective allylic alkylation of dioxanone substrates to prepare tertiary alcohols.
منابع مشابه
Enantioselective, convergent synthesis of the ineleganolide core by a tandem annulation cascade† †Electronic supplementary information (ESI) available: Experimental procedures, 1H NMR, 13C NMR, and IR spectra, X-ray crystallographic data. CCDC 853379, 1061009–1061014 and 1061016. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc03347d Click here for additional data file. Click here for additional data file.
An enantioselective and diastereoselective approach toward the synthesis of the polycyclic norditerpenoid ineleganolide is disclosed. A palladium-catalyzed enantioselective allylic alkylation is employed to stereoselectively construct the requisite chiral tertiary ether and facilitate the synthesis of a 1,3-cis-cyclopentenediol building block. Careful substrate design enabled the convergent ass...
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ورودعنوان ژورنال:
- Organic letters
دوره 14 22 شماره
صفحات -
تاریخ انتشار 2012