ChemInform Abstract: An Enantioselective Total Synthesis and Stereochemical Revision of (+)‐Citrinadin B.

• DOI: 10.1002/chin.201402204
• Publication Date: 2013-12-20T17:59:55Z
• Authors: Ke Kong; John A. Jr. Enquist; Monica E. McCallum; Genessa M. Smith; Takanori Matsumaru; Elnaz Menhaji‐Klotz; John L. Wood
• Keywords: Stereoisomerism; Organic Chemicals; 01 natural sciences; 6. Clean water; Indole Alkaloids; Substrate Specificity; 3. Good health; 0104 chemical sciences

This manuscript describes an enantioselective synthesis of the naturally occurring alkaloid citrinadin B. The synthetic effort revealed an anomaly in the original structural assignment that has led to the proposal of a stereochemical revision. This revision is consistent with the structures previously reported for a closely related family of alkaloids, PF1270A-C. The synthesis is convergent and employs a stereoselective intermolecular nitrone cyloaddition reaction as a key step.