FeCl3 Catalyzed Synthesis of cis-Fused Reduced THC Analogues

被引：0
|
作者：
Gurgone, Lucia [1 ]
Adessi, Tonino G. [1 ]
La-Venia, Agustina [1 ]
Gandon, Vincent [2 ]
Riveira, Martin J. [1 ]
机构：
[1] Univ Nacl Rosario, Fac Ciencias Bioquim & Farmaceut, Inst Quim Rosario, CONICET, Suipacha 531, RA-S2002LRK Rosario, Argentina
[2] Paris Saclay Univ, Inst Chim Mol & Mat Orsay, UMR CNRS 8182, Batiment Henri Moissan,17 Ave Sci, F-91400 Orsay, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 39期
关键词：
catalysis; heterocycles; Hetero-Diels Alder; natural products; THC analogues; ONE-POT SYNTHESIS; STRATEGY; CORE; MARINONE; CASCADE;
D O I：
10.1002/ejoc.202400608
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Studies on a cycloisomerization reaction of 2-prenylated-2H-pyrans towards cis-fused tetrahydro-6H-benzo[c]chromene systems (reduced cis-THC analogues) are reported. The transformation is catalyzed by iron chloride and proceeds with the formation of two new bonds and two stereocenters diastereoselectively. The same catalyst also promotes the formation of these products via a one-pot tandem Knoevenagel condensation of 1,3-cyclohexanediones and citral or farnesal aldehydes, followed by cycloisomerization establishing a direct assembly of this important scaffold.
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页数：8
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