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

ABSTRACT: [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.

SUBMITTER: Choi Y

PROVIDER: S-EPMC2587129 | biostudies-literature | 2005 Sep

REPOSITORIES: biostudies-literature

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

Choi Younggi Y Ishikawa Hayato H Velcicky Juraj J Elliott Gregory I GI Miller Michael M MM Boger Dale L DL

Organic letters 20050901 20

[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 tota ...[more]

PMID: 16178578

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Total synthesis of (-)- and ent-(+)-vindoline and related alkaloids.

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