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Literature DB >> 21291262

Asymmetric total synthesis of danicalipin A and evaluation of biological activity.

Taiki Umezawa¹, Masayuki Shibata, Kensuke Kaneko, Tatsufumi Okino, Fuyuhiko Matsuda.

Abstract

Asymmetric total synthesis of danicalipin A was achieved. The synthesis was characterized by diastereoselective introduction of chlorine atoms. Biological activities with synthetic danicalipin A, its enantiomer, and racemate were also evaluated toward brine shrimp. Both enantiomers of danicalipin A showed almost the same activity.

Entities: Chemical

Mesh：

Substances：
Lipids
danicalipin A

Year: 2011 PMID： 21291262 DOI： 10.1021/ol102882a

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

16 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

2. Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

Authors: Jakub Saadi; Matsujiro Akakura; Hisashi Yamamoto
Journal: J Am Chem Soc Date: 2011-08-18 Impact factor: 15.419

3. Synthesis of β-hydroxy-α-haloesters through super silyl ester directed syn-selective aldol reaction.

Authors: Susumu Oda; Hisashi Yamamoto
Journal: Org Lett Date: 2013-11-08 Impact factor: 6.005

4. Approaches to the chemical synthesis of the chlorosulfolipids.

Authors: Won-Jin Chung; Christopher D Vanderwal
Journal: Acc Chem Res Date: 2014-01-08 Impact factor: 22.384

5. Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.

Authors: Matthew L Landry; Dennis X Hu; Grace M McKenna; Noah Z Burns
Journal: J Am Chem Soc Date: 2016-04-08 Impact factor: 15.419

Asymmetric total synthesis of danicalipin A and evaluation of biological activity.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

3. Synthesis of β-hydroxy-α-haloesters through super silyl ester directed syn-selective aldol reaction.

4. Approaches to the chemical synthesis of the chlorosulfolipids.

5. Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.

Review 6. Catalytic Enantioselective Dihalogenation in Total Synthesis.

7. β-Siloxy-α-haloketones through highly diastereoselective single and double mukaiyama aldol reactions.

8. Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols.

9. A synthesis of the chlorosulfolipid mytilipin A via a longest linear sequence of seven steps.

10. The Alga Ochromonas danica Produces Bromosulfolipids.