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Lessons in Strain and Stability: Enantioselective Synthesis of (+)‐[5]‐Ladderanoic Acid
Author(s) -
Hancock Erin N.,
Kuker Erin L.,
Tantillo Dean J.,
Brown M. Kevin
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201910901
Subject(s) - enantioselective synthesis , cyclobutane , strain (injury) , chemistry , combinatorial chemistry , sequence (biology) , stereochemistry , catalysis , organic chemistry , biology , biochemistry , ring (chemistry) , anatomy
The synthesis of structurally complex and highly strained natural products provides unique challenges and unexpected opportunities for the development of new reactions and strategies. Herein, the synthesis of (+)‐[5]‐ladderanoic acid is reported. En route to the target, unusual and unexpected strain release driven transformations were uncovered. This occurrence required a drastic revision of the synthetic design that ultimately led to the development of a novel stepwise cyclobutane assembly by an allylboration/Zweifel olefination sequence.