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Total Synthesis of (−)‐Lundurine A and Determination of its Absolute Configuration
Author(s) -
Jin Shuaijiang,
Gong Jing,
Qin Yong
Publication year - 2015
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.201409963
Subject(s) - stereocenter , absolute configuration , ring (chemistry) , total synthesis , stereochemistry , absolute (philosophy) , chemistry , quaternary carbon , mathematics , enantioselective synthesis , organic chemistry , philosophy , catalysis , epistemology
A 15‐step total synthesis of (−)‐lundurine A ( 1 ) from easily accessible ( S )‐pyrrolidinone 18 is reported. A Simmons‐Smith reaction allows the efficient, simultaneous assembly of the cyclopropyl C ring, the six‐membered D ring, the seven‐membered E ring, and the quaternary carbon stereocenters at C2 and C7. The absolute configuration of natural (−)‐lundurine A was deduced to be 2 R ,7 R ,20 R based on the stepwise construction of the stereocenters during the total synthesis.