Literature DB >> 23039026

A torquoselective 6π electrocyclization approach to reserpine alkaloids.

Gregg A Barcan1, Ashay Patel, K N Houk, Ohyun Kwon.   

Abstract

A highly torquoselective thermal triene 6π electrocyclization controls the relative stereochemistry between the C3 and C18 stereocenters of the dodecahydroindolo[2,3-a]benzo[g]quinolizine skeleton of reserpine-type alkaloids. Employing a tandem cross-coupling/electrocyclization protocol allowed us to form the requisite triene and ensure its subsequent cyclization. A novel low-temperature dibromoketene acetal Claisen rearrangement established the requisite exocyclic dienylbromide precursor for the palladium-catalyzed cross-coupling reaction.

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Year:  2012        PMID： 23039026      PMCID： PMC3488149          DOI： 10.1021/ol302265z

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


  27 in total

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5.  Using theory and experiment to discover catalysts for electrocyclizations.

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6.  Reserpine exhumed.

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7.  Tandem 6pi-electrocyclization and cycloaddition of nitrodienes to yield multicyclic nitroso acetals.

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Review 4.  The expanding world of biosynthetic pericyclases: cooperation of experiment and theory for discovery.

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6.  Synthesis of ent-ketorfanol via a C-H alkenylation/torquoselective 6π electrocyclization cascade.

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7.  Origins of 1,6-stereoinduction in torquoselective 6π electrocyclizations.

Authors:  Ashay Patel; Gregg A Barcan; Ohyun Kwon; K N Houk
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8.  Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.

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9.  Enantioselective total synthesis of (+)-reserpine.

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10.  A Concise, Enantioselective Approach for the Synthesis of Yohimbine Alkaloids.

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