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Literature DB >> 24058215

Concise enantioselective synthesis of diospongins A and B.

Eric Stefan¹, Ansel P Nalin, Richard E Taylor.

Abstract

Ether transfer methodology is capable of stereoselectively generating 1,3-diol mono- and diethers in good yield. Surprisingly, allylic and benzylic substrates provide none of the desired products when exposed to previously optimized conditions of iodine monochloride. Herein, second-generation activation conditions for ether transfer have been developed that circumvents undesired side reactions for these substrates. The application of this chemistry to the enantioselective synthesis of diospongins A and B has now been accomplished.

Entities: CellLine Chemical Disease Species

Keywords: Antiosteoporotic activity; Diospongin; Ether transfer; Radical cyclization

Year: 2013 PMID： 24058215 PMCID： PMC3775279 DOI： 10.1016/j.tet.2013.05.081

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

11 in total

1. New diarylheptanoids from the rhizomes of Dioscorea spongiosa and their antiosteoporotic activity.

Authors: Jun Yin; Kyoji Kouda; Yasuhiro Tezuka; Quan Le Tran; Tatsuro Miyahara; Yingjie Chen; Shigetoshi Kadota
Journal: Planta Med Date: 2004-01 Impact factor: 3.352

2. Toward an enantioselective synthesis of (-)-zampanolide: preparation of the C9-C20 region.

Authors: Matthew R Wilson; Richard E Taylor
Journal: Org Lett Date: 2012-06-21 Impact factor: 6.005

3. Electrophile-induced ether transfer: a new approach to polyketide structural units.

Authors: Kai Liu; Richard E Taylor; Rendy Kartika
Journal: Org Lett Date: 2006-11-09 Impact factor: 6.005

4. Electrophile-induced ether transfer: stereoselective synthesis of 2,4,6-trisubstituted tetrahydropyrans.

Authors: Rendy Kartika; Richard E Taylor
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

5. A flexible enantioselective total synthesis of diospongins A and B and their enantiomers using catalytic hetero-Diels-Alder/Rh-catalyzed 1,4-addition and asymmetric transfer hydrogenation reactions as key steps.

Authors: Gullapalli Kumaraswamy; Gajula Ramakrishna; Police Naresh; Bharatam Jagadeesh; Balasubramanian Sridhar
Journal: J Org Chem Date: 2009-11-06 Impact factor: 4.354

6. Application of stereoselective ether transfer to the synthesis of isotactic polyethers.

Authors: Kai Liu; Joseph W Arico; Richard E Taylor
Journal: J Org Chem Date: 2010-06-18 Impact factor: 4.354

7. Efficient total syntheses and structural verification of both diospongins A and B via a common delta-lactone intermediate.

Authors: Kailas B Sawant; Michael P Jennings
Journal: J Org Chem Date: 2006-09-29 Impact factor: 4.354

2. The stereodivergent formation of 2,6-cis and 2,6-trans-tetrahydropyrans: experimental and computational investigation of the mechanism of a thioester oxy-Michael cyclization.

Authors: Kristaps Ermanis; Yin-Ting Hsiao; Uğur Kaya; Alan Jeuken; Paul A Clarke
Journal: Chem Sci Date: 2016-08-30 Impact factor: 9.825

2 in total

Concise enantioselective synthesis of diospongins A and B.

1. New diarylheptanoids from the rhizomes of Dioscorea spongiosa and their antiosteoporotic activity.

2. Toward an enantioselective synthesis of (-)-zampanolide: preparation of the C9-C20 region.

3. Electrophile-induced ether transfer: a new approach to polyketide structural units.

4. Electrophile-induced ether transfer: stereoselective synthesis of 2,4,6-trisubstituted tetrahydropyrans.

5. A flexible enantioselective total synthesis of diospongins A and B and their enantiomers using catalytic hetero-Diels-Alder/Rh-catalyzed 1,4-addition and asymmetric transfer hydrogenation reactions as key steps.

6. Application of stereoselective ether transfer to the synthesis of isotactic polyethers.

7. Efficient total syntheses and structural verification of both diospongins A and B via a common delta-lactone intermediate.

8. Stereoselective synthesis of the C9-C19 fragment of lyngbyaloside B and C via ether transfer.

9. Concise enantioselective total synthesis of neopeltolide macrolactone highlighted by ether transfer.

10. Electrophile-induced ether transfer: stereoselective synthesis of 2,6-disubstituted-3,4-dihydropyrans.

1. Total Synthesis and Structural Reassignment of Lyngbyaloside C Highlighted by Intermolecular Ketene Esterification.

2. The stereodivergent formation of 2,6-cis and 2,6-trans-tetrahydropyrans: experimental and computational investigation of the mechanism of a thioester oxy-Michael cyclization.