194931-12-9Relevant academic research and scientific papers
The enantioselective total synthesis of (-)-myltaylenol
Doye, Sven,Hotopp, Torsten,Wartchow, Rudolf,Winterfeldt, Ekkehard
, p. 1480 - 1488 (1998)
The unusual sesquiterpenoid alcohol (-)-myltaylenol (1) is synthesized by an intramolecular [4+2] cycloaddition of a chiral diene accessible from Hajos-Wiechert ketone by a sequence of reactions including stereoselective alkylation of an unsaturated ketone with thiophenylmethyl iodide as alkylation agent. As the link between diene and olefin a sulfonic ester group is used. The link permits control of the stereoselectivity of the [4+2] cycloaddition. After this key step the sulfonic ester group can be removed under oxidative conditions by molecular oxygen as oxidation agent, leading directly to a hydroxyketone that can be converted to (-)-myltaylenol by successive Shapiro reaction, regioselective hydroboration and Wittig reaction.
The enantioselective total synthesis of (-)-myltaylenol
Doye, Sven,Hotopp, Torsten,Winterfeldt, Ekkehard
, p. 1491 - 1492 (2007/10/03)
Using an intramolecular Diels-Alder cycloaddition followed by an oxidative rupture of the connective unit as the key step, the unusual carbon framework of (-)-myltaylenol was established.
