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Literature DB >> 27933858

Stereocontrolled Formation of a [4.4]Heterospiro Ring System with Unexpected Inversion of Configuration at the Spirocenter.

Abstract

Stereoselective construction of the 1,3-diazaspiro[4.4]nonane core skeleton of massadine and related dimeric pyrrole-imidazole alkaloids is a synthetic challenge. We describe herein the synthesis of all C13/14 diastereomers of this spiro molecule through controlled oxidation and epimerization of the C13 spirocenter under mild acidic conditions.

Entities: Chemical Disease Gene

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Year: 2016 PMID： 27933858 PMCID： PMC5527678 DOI： 10.1021/acs.joc.6b02266

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

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References

37 in total

1. Facile synthesis of the trans-fused azabicyclo[3.3.0]octane core of the palau'amines and the tricyclic core of the axinellamines from a common intermediate.

Authors: Manuel A Zancanella; Daniel Romo
Journal: Org Lett Date: 2008-08-12 Impact factor: 6.005

2. Regiocontrol in Mn(III)-mediated oxidative heterobicyclizations: access to the core skeletons of oroidin dimers.

Authors: Xianghui Tan; Chuo Chen
Journal: Angew Chem Int Ed Engl Date: 2006-06-26 Impact factor: 15.336

3. Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines.

Authors: Ian B Seiple; Shun Su; Ian S Young; Akifumi Nakamura; Junichiro Yamaguchi; Lars Jørgensen; Rodrigo A Rodriguez; Daniel P O'Malley; Tanja Gaich; Matthias Köck; Phil S Baran
Journal: J Am Chem Soc Date: 2011-08-23 Impact factor: 15.419

Review 4. Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

Authors: Ali Al-Mourabit; Manuel A Zancanella; Supriya Tilvi; Daniel Romo
Journal: Nat Prod Rep Date: 2011-05-09 Impact factor: 13.423

Stereocontrolled Formation of a [4.4]Heterospiro Ring System with Unexpected Inversion of Configuration at the Spirocenter.

1. Facile synthesis of the trans-fused azabicyclo[3.3.0]octane core of the palau'amines and the tricyclic core of the axinellamines from a common intermediate.

2. Regiocontrol in Mn(III)-mediated oxidative heterobicyclizations: access to the core skeletons of oroidin dimers.

3. Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines.

Review 4. Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

5. Revisiting the Kinnel-Scheuer hypothesis for the biosynthesis of palau'amine.

6. Massadine, a novel geranylgeranyltransferase type I inhibitor from the marine sponge Stylissa aff. massa.

7. Synthesis of the Carbocyclic Core of Massadine.

8. Oxidative rearrangement of imidazoles with dimethyldioxirane.

Review 9. A submarine journey: the pyrrole-imidazole alkaloids.

10. Total synthesis of palau'amine.