Facile Multistep Synthesis of Isotruxene and Isotruxenone | Zendy

JyeShane Yang | Zendy; Hsin-Hau Huang | Zendy; ShihHsun Lin | Zendy

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Facile Multistep Synthesis of Isotruxene and Isotruxenone

Author(s) -

JyeShane Yang,

Hsin-Hau Huang,

ShihHsun Lin

Publication year - 2009

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo900299q

Subject(s) - regioselectivity , yield (engineering) , intramolecular force , friedel–crafts reaction , acylation , chemistry , conjugated system , column chromatography , combinatorial chemistry , catalysis , organic chemistry , materials science , polymer , metallurgy

Three multistep approaches toward facile syntheses of isotruxene (1) and isotruxenone (3) are reported. The ortho-para conjugated backbone in the precursor 4 was constructed by either Co-catalyzed [2 + 2 + 2] cyclotrimerization or the [4 + 2] Diels-Alder reactions. The regioselectivity of the triple intramolecular Friedel-Crafts acylation of 4 plays the key role in determining the overall yield. Compared to the previous one-step method, the current approaches are more efficient in terms of product yield (27-36% vs 4-18%) and purification (i.e., free of column chromatography).

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