Studies toward the total synthesis of nominine.
The construction of the hetisane group of alkaloids, of which the extensively bridged nominine 17 is the simplest member, poses the ultimate challenge for those interested in the synthesis of the C20 diterpene alkaloids. We describe the synthesis of an advanced intermediate toward this goal. The key steps include reductive acylation, reductive deoxygenation, Birch reduction, and an intramolecular Lewis acid-catalyzed 1,6-addition of a carbamate to a dienone.
Hutt
Oliver E
OE
Research School of Chemistry, The Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia. huttx005@umn.edu
Mander
Lewis N
LN
D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D004224:Diterpenes; D007211:Indoles; C473425:nominine