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Total Synthesis of Gracilamine
Author(s) -
Shi Yingbo,
Yang Baochao,
Cai Shujun,
Gao Shuanhu
Publication year - 2014
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/anie.201405418
Subject(s) - intramolecular force , total synthesis , amaryllidaceae alkaloids , chemistry , stereochemistry , mannich reaction , amaryllidaceae , alkaloid , combinatorial chemistry , organic chemistry , catalysis , biology , botany
The total synthesis of gracilamine, a pentacyclic Amaryllidaceae alkaloid, was achieved from simple building blocks. The synthesis features a mild photo‐Nazarov reaction, intramolecular 1,4‐addition, and an intramolecular Mannich reaction. This approach not only confirms the C6 stereochemistry of natural gracilamine, and also provides a novel solution to prepare its derivatives and structurally related natural products.
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