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Unified Total Synthesis of Hetiamacins A–D
Author(s) -
Tsukaguchi Shogo,
Enomoto Masaru,
Towada Ryo,
Ogura Yusuke,
Kuwahara Shigefumi
Publication year - 2019
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.201901114
Subject(s) - chemistry , moiety , enantioselective synthesis , total synthesis , stereochemistry , ring (chemistry) , lactone , derivative (finance) , sequence (biology) , combinatorial chemistry , organic chemistry , catalysis , biochemistry , financial economics , economics
A concise enantioselective total synthesis of hetiamacin A has been accomplished from a known l ‐aspartic acid derivative by an eight‐step sequence that features ammonolytic opening of the γ‐lactone moiety of amicoumacin C followed by 1,3‐oxazinane ring formation in one pot. Hetiamacins B–D with putatively assigned stereochemistries have also been synthesized from amicoumacin C, each in three steps involving tetrahydro‐4(1 H )‐pyrimidinone ring formation. The excellent NMR spectroscopic agreement of the synthetic materials with the corresponding natural products, coupled with biosynthetic considerations, has enabled the full stereochemical assignments of hetiamacins B–D.