Total synthesis of (+/-)-powelline and (+/-)-buphanidrine.

Journal article

The total synthesis of (+/-)-powelline (13 linear steps in an overall yield of 6%) and (+/-)-buphanidrine (14 linear steps and a 6% overall yield) and has been achieved using a novel approach to the crinane skeleton. An organocatalytic oxidative coupling allowed direct construction of the key quaternary carbon-to-aryl bond in high yield allowing rapid access to the target alkaloids.

Authors: Bogle, K; Hirst, D; Dixon, D

• Publication status: Published
• Journal: Organic letters
• Volume: 12
• Issue: 6
• Pages: 1252-1254
• Publication date: 2010-03-01
• DOI: 10.1021/ol1000654
• EISSN: 1523-7052
• ISSN: 1523-7060
• Language: English
• Keywords: Phenanthridines; Stereoisomerism; Crystallography, X-Ray; Models, Molecular; Molecular Structure; Liliaceae; Amaryllidaceae Alkaloids