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Stereodivergent and Reiterative Synthesis of Bistetrahydrofuran Ring Cores of Annonaceous Acetogenins
Author(s) -
Kojima Naoto,
Maezaki Naoyoshi,
Tominaga Hiroaki,
Yanai Minori,
Urabe Daisuke,
Tanaka Tetsuaki
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200305459
Subject(s) - diastereomer , acetogenin , ring (chemistry) , tetrahydrofuran , stereochemistry , alkynylation , chemistry , organic chemistry , catalysis , biology , botany , annonaceae , solvent
Eight diastereoisomers of the bistetrahydrofuran ring cores of annonaceous acetogenins have been synthesized by asymmetric alkynylation of α‐tetrahydrofuranic aldehydes and stereodivergent one‐pot tetrahydrofuran (THF) ring formation. In all cases, the asymmetric alkynylation proceeded with very high diastereoselectivity to give eight kinds of optically pure THF cores. We also describe a comparison of the 1 H and 13 C NMR spectral data of the eight isomers and give full details of the THF ring construction.