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Polycyclic Molecules from Linear Precursors: Stereoselective Synthesis of Clavolonine and Related Complex Structures
Author(s) -
Evans David A.,
Scheerer Jonathan R.
Publication year - 2005
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.200502296
Subject(s) - intramolecular force , stereoselectivity , chemistry , stereochemistry , carbon chain , total synthesis , cascade , molecule , organic chemistry , catalysis , chromatography
A clever way to clavolonine : The total synthesis of the lycopodium alkaloid clavolonine ( 2 ) from a linear precursor 1 that contains the complete 16‐carbon‐atom chain is reported (see scheme). Intramolecular and transannular cascade reaction sequences are explored from both linear and macrocyclic precursors. A variety of polycyclic structures are rapidly constructed from simple acyclic precursors.