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Total synthesis of (−)-vindoline
- Chen, Wen, Tian, Hongchang, Tan, Wenyun, Liu, Xiaotong, Yang, Xiaodong, Zhang, Hongbin
- Tetrahedron 2019 v.75 no.12 pp. 1751-1759
- Bronsted acids, carbon, chemical reactions, chemical structure, diastereoselectivity, organic compounds, stereochemistry
- In this full paper, a stereocontrolled strategy for the total synthesis of (−)-vindoline is described. This synthetic route features: 1) rapid construction of the stereochemical center at C19 through a highly diastereoselective vinylogous Mannich addition; 2) tandem Heathcock/aza-Prins cyclization to install rings C and E in vindoline; 3) oxidative transformation of β-ketoester to enone; 4) stereoselective inversion of C4 stereochemistry with triphenylphosphine and carbon tetrabromide followed by Brønsted acid.