Total synthesis of (-)- and ent-(+)-vindoline

• Published in: Organic letters Vol. 7; no. 20; pp. 4539 - 4542
• Main Authors: Choi, Younggi, Ishikawa, Hayato, Velcicky, Juraj, Elliott, Gregory I, Miller, Michael M, Boger, Dale L
• Format: Journal Article
• Language: English
• Published: United States 29-09-2005
• Subjects: Biological Products - chemistry; Molecular Structure; Stereoisomerism; Vinblastine - analogs & derivatives; Vinblastine - chemical synthesis; Vinblastine - chemistry
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol051975x

[reaction: see text] Two exceptionally concise total syntheses of (-)- and ent-(+)-vindoline are detailed enlisting a diastereoselective tandem [4 + 2]/[3 + 2] cycloaddition of a 1,3,4-oxadiazole. The unique reaction cascade assembles the fully functionalized pentacyclic ring system of vindoline in a single step that forms four C-C bonds and three rings while introducing all requisite functionality and setting all six stereocenters within the central ring including three contiguous and four total quaternary centers.