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Total Synthesis of the Antitumor Depsipeptide FE399 and Its S‐Benzyl Derivative: A Macrolactamization Approach
Author(s) -
Tonoi Takayuki,
Ikeda Miyuki,
Sato Teruyuki,
Inohana Takehiko,
Kawahara Ryo,
Murata Takatsugu,
Shiina Isamu
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000459
Subject(s) - depsipeptide , chemistry , moiety , derivative (finance) , natural product , stereochemistry , total synthesis , combinatorial chemistry , economics , financial economics
An efficient and practical method for the synthesis of (9 R ,14 R ,17 R )‐FE399, a novel antitumor bicyclic depsipeptide, was developed. A 2‐methyl‐6‐nitrobenzoic anhydride (MNBA)‐mediated dehydration condensation reaction was effectively employed for the formation of the 16‐membered macrocyclic depsipeptide moiety of FE399. FE399 was found to exist as an inseparable equilibrium mixture of conformational isomers; the mixture was quantitatively transformed into the corresponding S ‐benzyl product and isolated as a single isomer. Thus, we could confirm that the molecular structure of FE399 obtained by this method is identical to that of the natural product.