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Literature DB >> 20178342

A tandem Prins/Schmidt reaction approach to marine alkaloids: formal and total syntheses of lepadiformines A and C.

Angelica M Meyer¹, Christopher E Katz, Sze-Wan Li, David Vander Velde, Jeffrey Aubé.

Abstract

The tricyclic core of the cylindricine or lepadiformine families of alkaloid natural products was assembled via a Prins addition/intramolecular Schmidt rearrangement under Lewis acid conditions. Both single-pot and two-stage variations of this process were examined, with particular attention to the stereochemical outcome of the processes. This technology has been applied to a formal total synthesis of lepadiformine A and a total synthesis of lepadiformine C.

Entities: Chemical Disease Gene

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Year: 2010 PMID： 20178342 PMCID： PMC2846845 DOI： 10.1021/ol100113r

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

21 in total

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5. Epoxide-initiated electrophilic cyclization of azides: a novel route for the stereoselective construction of azabicyclic ring systems and total synthesis of (+/-)-indolizidine 167B and 209D.

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6. Domino reactions that combine an azido-Schmidt ring expansion with the Diels-Alder reaction.

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7. Domino electrocyclization/azide-capture/schmidt rearrangement of dienones: one-step synthesis of dihydropyridones from simple building blocks.

Authors: Dong Song; Ali Rostami; F G West
Journal: J Am Chem Soc Date: 2007-09-08 Impact factor: 15.419

8. Epoxide-initiated cationic cyclization of azides: a novel method for the stereoselective construction of 5-hydroxymethyl azabicyclic compounds and application in the stereo- and enantioselective total synthesis of (+)- and (-)-indolizidine 167B and 209D.

Authors: P Ganapati Reddy; Sundarababu Baskaran
Journal: J Org Chem Date: 2004-04-30 Impact factor: 4.354

9. Diastereoselective Prins-type reaction of cycloalkenylcyclopropanol silyl ethers and alpha,beta-unsaturated aldehyde acetals.

Authors: Ivan L Lysenko; Heong-Sub Oh; Jin Kun Cha
Journal: J Org Chem Date: 2007-09-13 Impact factor: 4.354

10. Utilization of a Michael addition: dipolar cycloaddition cascade for the synthesis of (+/-)-cylindricine C.

Authors: Andrew C Flick; Maria José Arevalo Caballero; Albert Padwa
Journal: Org Lett Date: 2008-04-10 Impact factor: 6.005

6 in total

1. Fully substituted carbon centers by diastereoselective spirocyclization: stereoselective synthesis of (+)-lepadiformine C.

Authors: Matthew A Perry; Matthew D Morin; Brian W Slafer; Scott A Wolckenhauer; Scott D Rychnovsky
Journal: J Am Chem Soc Date: 2010-07-21 Impact factor: 15.419