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The Total Synthesis of Chondrochloren A
Author(s) -
Linne Yannick,
Bonandi Elisa,
Tabet Christopher,
Geldsetzer Jan,
Kalesse Markus
Publication year - 2021
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.202016072
Subject(s) - total synthesis , amide , polyketide , vinyl bromide , chemistry , combinatorial chemistry , stereochemistry , bromide , transformation (genetics) , coupling reaction , organic chemistry , catalysis , biosynthesis , biochemistry , gene , enzyme
The first total synthesis of chondrochloren A is accomplished using a 1,2‐metallate rearrangement addition as an alternative for the Nozaki‐Hiyama‐Kishi reaction. This transformation also avoids the inherent challenges of this polyketide segment and provides a new, unprecedented strategy to assemble polyketidal frameworks. The formation of the Z‐enamide is accomplished using a Z‐selective cross coupling of the corresponding amide to a Z‐vinyl bromide.