Literature DB >> 11671581

A Concise and Convenient Synthesis of DL-proto-Quercitol and DL-gala-Quercitol via Ene Reaction of Singlet Oxygen Combined with [2 + 4] Cycloaddition to Cyclohexadiene.

Emine Salamci1, Hasan Seçen, Yasar Sütbeyaz, Metin Balci.   

Abstract

Photooxygenation of 1,4-cyclohexadiene afforded hydroperoxy endoperoxides 3 and 4 in a ratio of 88:12. Reduction of 3 with LiAlH(4) or thiourea followed by acetylation of the hydroxyl group and KMnO(4) oxidation of the double bond gave proto-quercitol 10b. Application of the same reaction sequences to 4 resulted in the formation of gala-quercitol 14. Quercitols were easily obtained by ammonolysis of acetate derivatives in MeOH. The outcome of dihydroxylation reactions were supported by conformational analysis.

Entities:  

Year:  1997        PMID： 11671581     DOI： 10.1021/jo962092+

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

1.  Endogenously synthesized (-)-proto-quercitol and glycine betaine are principal compatible solutes of Schizochytrium sp. strain S8 (ATCC 20889) and three new isolates of phylogenetically related thraustochytrids.

Authors:  Anita N Jakobsen; Inga M Aasen; Arne R Strøm
Journal:  Appl Environ Microbiol       Date:  2007-07-27       Impact factor: 4.792

2.  Polar compounds isolated from the leaves of Albertisia delagoensis (Menispermaceae).

Authors:  Geoffrey E Hawkes; Helene de Wet; Jia Li
Journal:  Molecules       Date:  2011-11-02       Impact factor: 4.411

Review 3.  Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches.

Authors:  Rodrigo Costa E Silva; Luely Oliveira da Silva; Aloisio de Andrade Bartolomeu; Timothy John Brocksom; Kleber Thiago de Oliveira
Journal:  Beilstein J Org Chem       Date:  2020-05-06       Impact factor: 2.883

4.  Ground-state dioxygen undergoes metal-free [3 + 2]-annulations with allenes and nitrosoarenes under ambient conditions.

Authors:  Jinxian Liu; Manisha Skaria; Pankaj Sharma; Yun-Wei Chiang; Rai-Shung Liu
Journal:  Chem Sci       Date:  2017-05-24       Impact factor: 9.825
  4 in total

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