130982-23-9Relevant academic research and scientific papers
A new approach to (±)-heritonin. The preparation of β-tetralones from allylsilanes and acid chlorides
Silveira, Claudio C.,Machado, Alessandra,Braga, Antonio L.,Lenard?o, Eder Jo?o
, p. 4077 - 4080 (2004)
A new method for the preparation of 4-alkyl-β-tetralones is described, by reaction of arylacetic acid chlorides with allylsilanes. Employing β-tetralone 5, the synthesis of (±)-heritonine and (±)-epi-heritonine, natural piscicides isolated from Heritiera littoralis, was achieved in four steps and 22% overall yield. The key step of this synthesis involved the selenocarbenium ion-mediated elaboration of the butenolide ring of the natural product.
A highly diastereoselective total synthesis of (±)-heritonin and (±)-heritol
Chavan, Subhash P.,Garai, Sumanta,Kalkote, Uttam R.
, p. 8509 - 8514 (2012/10/08)
A highly diastereoselective synthesis of heritol and heritonin by intramolecular cyclization on a preformed sensitive butenolide functionality is described. Graphical abstract:
Cu(II)-catalyzed acylation by thiol esters under neutral conditions: Tandem acylation-wittig reaction leading to a one-pot synthesis of butenolides
Matsuo, Kazumasa,Shindo, Mitsuru
supporting information; experimental part, p. 5346 - 5349 (2011/01/05)
The first catalytic acylation of alcohols with a thiol ester present in Wittig reagents under neutral conditions catalyzed by the Cu(II) salt through a push-pull mechanism is reported. Furthermore, a new methodology for the one-pot lactonization of acyloins by a copper catalyst is developed. The synthetic utility of this method for the synthesis of natural products is shown.
SYNTHESIS OF (+/-)-HERITOL
Zubaidha, P. K.,Chavan, Subhash P.,Racheria, Uday S.,Ayyangar, Nagaraj R.
, p. 5759 - 5768 (2007/10/02)
Synthesis of (+/-)-heritol and epi-heritol is described.The key step is the osmylation of the unsaturated ester 9a.Osmylation is used as a tool to construct the α,β-unsaturated γ-lactone system.
