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Bioinspired Total Synthesis of Agelastatin A
Author(s) -
Reyes Jeremy Chris P.,
Romo Daniel
Publication year - 2012
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.201200959
Subject(s) - library science , chemistry , computer science
A one‐two punch : Two potentially biosynthetically relevant cyclizations of a keramadine analogue give agelastatin A (see scheme). A diastereoselective C‐ring formation, which proceeds through a 5‐ exo ‐trig cyclization or a Nazarov cyclization of a red‐colored N ‐acyliminium intermediate, generates the three contiguous stereocenters of the cyclopentane core. A silica gel assisted cyclization of a nagelamide J analogue gives agelastatin A.