Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom