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Literature DB >> 20192209

Ga(III)-catalyzed cycloisomerization approach to (+/-)-icetexone and (+/-)-epi-icetexone.

Felipe de Jesus Cortez¹, Richmond Sarpong.

Abstract

A Ga(III)-catalyzed cycloisomerization reaction provides expedient access to a benzannulated cycloheptadiene bearing a cyano group, which has been applied to the syntheses of several icetexane diterpenoids including icetexone and epi-icetexone. Key to the synthesis is a novel in situ generated diazene rearrangement.

Entities: Chemical Disease Species

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Year: 2010 PMID： 20192209 PMCID： PMC2853035 DOI： 10.1021/ol902959v

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

8 in total

1. Rapid construction of the cortistatin pentacyclic core.

Authors: Eric M Simmons; Alison R Hardin; Xuelei Guo; Richmond Sarpong
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

Review 2. Structure, biosynthetic relationships and chemical synthesis of the icetexane diterpenoids.

Authors: Eric M Simmons; Richmond Sarpong
Journal: Nat Prod Rep Date: 2009-06-25 Impact factor: 13.423

3. Icetexane and abietane diterpenoids from Salvia gilliessi.

Authors: M Nieto; E E García; O S Giordano; C E Tonn
Journal: Phytochemistry Date: 2000-04 Impact factor: 4.072

4. A novel icetexane diterpene, 5-epi-icetexone from Salvia gilliessi is active against Trypanosoma cruzi.

Authors: A M Sanchez; V Jimenez-Ortiz; T Sartor; C E Tonn; E E García; M Nieto; M H Burgos; M A Sosa
Journal: Acta Trop Date: 2006-05-02 Impact factor: 3.112

5. Ga(III)-catalyzed cycloisomerization strategy for the synthesis of icetexane diterpenoids: total synthesis of (+/-)-salviasperanol.

Authors: Eric M Simmons; Richmond Sarpong
Journal: Org Lett Date: 2006-06-22 Impact factor: 6.005

6. Skeletal reorganization of enynes catalyzed by InCl3.

Authors: Yuhei Miyanohana; Naoto Chatani
Journal: Org Lett Date: 2006-05-11 Impact factor: 6.005

7. Total synthesis of (+)-19-deoxyicetexone, (-)-icetexone, and (+)-5-epi-icetexone.

Authors: George Majetich; Jeremy L Grove
Journal: Org Lett Date: 2009-07-02 Impact factor: 6.005

8. Reconciling icetexane biosynthetic connections with their chemical synthesis: total synthesis of (+/-)-5,6-dihydro-6alpha-hydroxysalviasperanol, (+/-)-brussonol, and (+/-)-abrotanone.

Authors: Eric M Simmons; Jennifer R Yen; Richmond Sarpong
Journal: Org Lett Date: 2007-06-09 Impact factor: 6.005

8 in total

5 in total

Review 1. Transition Metal Catalysis Controlled by Hydrogen Bonding in the Second Coordination Sphere.

Authors: Joost N H Reek; Bas de Bruin; Sonja Pullen; Tiddo J Mooibroek; Alexander M Kluwer; Xavier Caumes
Journal: Chem Rev Date: 2022-05-20 Impact factor: 72.087

2. Gallium(III)-catalyzed cycloisomerization approach to the diterpenoid alkaloids: construction of the core structure for the hetidines and hetisines.

Authors: Amy M Hamlin; Felipe de Jesus Cortez; David Lapointe; Richmond Sarpong
Journal: Angew Chem Int Ed Engl Date: 2013-03-26 Impact factor: 15.336

3. Synthetic studies on the icetexones: enantioselective formal syntheses of icetexone and epi-icetexone.

Authors: Felipe de Jesus Cortez; David Lapointe; Amy M Hamlin; Eric M Simmons; Richmond Sarpong
Journal: Tetrahedron Date: 2013-07-08 Impact factor: 2.457

4. Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors: Ruth Dorel; Antonio M Echavarren
Journal: Chem Rev Date: 2015-04-06 Impact factor: 60.622

5. Studies on C20-diterpenoid alkaloids: synthesis of the hetidine framework and its application to the synthesis of dihydronavirine and the atisine skeleton.

Authors: Amy M Hamlin; David Lapointe; Kyle Owens; Richmond Sarpong
Journal: J Org Chem Date: 2014-07-11 Impact factor: 4.354

5 in total