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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 54, Number 3
JKCSEZ 54(3)
June 20, 2010 

Organic Synthesis Based on Ruthenium Carbene Catalyzed Metathesis Reactions and Pyridinium Salt Photochemistry

루테늄 카벤 촉매 복분해 상호교환 반응과 피리듐 염 광화학반응을 이용한 유기 합성
Dae Won Cho, Patrick S Mariano*

조대원, Patrick S Mariano*
고리전이 복분해 반응, 다이엔아인 복분해 반응, 광화학, 천연물 합성 , Ring rearrangement metathesis, Dienyne metathesis, Photochemistry, Natural product synthesis

In this account, three synthetic methodologies that serve as the basis for new strategies for the preparation of selected natural products are briefly introduced. One process, involving ruthenium carbene catalyzed ring rearrangement metathesis developed by Grubbs and his coworkers, transforms alkene-tethered cycloalkenes to thermodynamically more favored alkene-tethered cycloalkenes. Another ruthenium carbene promoted reaction, referred to as dienyne metathesis, was uncovered in early studies by Grubbs and his collaborators. This process converts dienynes to fused bicyclic conjugated dienes. Finally, a novel photo-electrocyclization reaction of pyridinium salts, which leads to the formation of 4-aminocyclopenten-3,5-diol derivatives, is discussed. Examples are provided to show the utility of these methodologies in natural product synthesis. Emphasis is given to studies in which pyridinium salt photochemistry is coupled with ring rearrangement and dienyne metathesis in routes for the synthesis of polyhydroxyalted indolizidine alkaloids and the construction of the tricyclic core of the lepadiformine and cylindricine alkaloids.

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