99237-58-8Relevant academic research and scientific papers
Stereospecific Synthesis of Dienes and Trienes from Pyrylium Perchlorate: a Convergent Approach to Leukotrienes
Furber, Mark,Taylor, Richard J. K.
, p. 782 - 783 (1985)
A range of conjugated dienes and trienes have been prepared in a stereospecific manner by the treatment of pyrylium perchlorate with organolithium reagents; model studies have been carried out which demonstrate the suitability of this methodology for the
Stereoselective Synthesis of 2Z,4E-Dienals by Addition of Organometallic Reagents to Pyrylium Perchlorate
Furber, Mark,Herbert, John M.,Taylor, Richard J. K.
, p. 683 - 690 (2007/10/02)
A facile and stereoselective approach to 2Z,4E-dienals and derived products is presented.The method involves addition of an organometallic reagent to a pyrylium salt, followed by electrocyclic ring-opening of the intermediate 2H-pyran, to give the desired Z,E-dienal, usually with greater than 95percent stereochemical purity.These dienals may be trapped in situ with a second organometallic reagent, or oxidised or redused, without loss of stereochemical integrity.The synthesis of (1,3Z,5E)-undeca-1,3,5-triene, a component of the essential oils of the brown Hawaiian seaweeds Dictyopteris plagiogramma and D. australis, is reported to illustrate the simplicity of the procedure.
