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A Concise Formal Total Synthesis of (±)‐Strychnine by Using a Transannular Inverse‐Electron‐Demand Diels–Alder Reaction of a [3](1,3)Indolo[3](3,6)pyridazinophane
Author(s) -
Bodwell Graham J.,
Li Jiang
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020902)41:17<3261::aid-anie3261>3.0.co;2-k
Subject(s) - strychnine , inverse , chemistry , diels–alder reaction , stereochemistry , computer science , organic chemistry , mathematics , catalysis , biochemistry , geometry
(±)‐Strychnine in 12 easy steps! This concise synthesis involves the construction of a [3.3]cyclophane and its transannular inverse‐electron‐demand Diels–Alder reaction to afford a pentacycle quantitatively (see scheme), which is rapidly converted into Rawal's key ABCEG intermediate; thus (±)‐strychnine can be synthesized from tryptamine in only 12 steps.