1319726-69-6Relevant articles and documents
Asymmetric total synthesis of (?)-melotenine A
Zhao, Senzhi,Sirasani, Gopal,Vaddypally, Shivaiah,Zdilla, Michael J.,Andrade, Rodrigo B.
, p. 6107 - 6112 (2016)
We have developed a sequential one-pot Mitsunobu/intramolecular aza-Baylis–Hillman reaction to construct the ABCE tetracyclic core of the Strychnos alkaloids and applied this method to the total synthesis of (?)-melotenine A (1), a novel rearranged Aspidosperma alkaloid with potent cytotoxic activity. Additional key steps in the synthesis included (1) a Piers annulation of a vinyl iodide and a methyl ketone to prepare the D ring and (2) a site-selective intermolecular vinylogous aldol reaction to functionalize the E ring.
Total synthesis of (-)-melotenine A
Zhao, Senzhi,Sirasani, Gopal,Vaddypally, Shivaiah,Zdilla, Michael J.,Andrade, Rodrigo B.
, p. 8309 - 8311 (2013)
'Melo' out: A concise asymmetric synthesis of (-)-melotenine A has been accomplished in fourteen steps and 1 % overall yield from commercial N-tosylindole-3-carboxaldehyde. Key steps include a Piers annulation, an intermolecular vinylogous aldol reaction, and a novel one-pot sequence to prepare the ABCE tetracycle. Boc=tert-butoxycarbonyl, Ts=4-toluenesulfonyl. Copyright