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Systematic Construction of a Monotetrahydrofuran‐Ring Library in Annonaceous Acetogenins by Asymmetric Alkynylation and Stereodivergent Tetrahydrofuran‐Ring Formation
Author(s) -
Kojima Naoto,
Maezaki Naoyoshi,
Tominaga Hiroaki,
Asai Mikito,
Yanai Minori,
Tanaka Tetsuaki
Publication year - 2003
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.200305185
Subject(s) - tetrahydrofuran , alkynylation , acetogenin , diastereomer , ring (chemistry) , chemistry , stereochemistry , organic chemistry , catalysis , botany , biology , annonaceae , solvent
All eight diastereoisomers of the monotetrahydrofuran‐ring cores of annonaceous acetogenins have been synthesized through utilization of asymmetric alkynylation and stereodivergent one‐pot tetrahydrofuran‐ring formation. In all cases, the asymmetric alkynylation proceeded with very high diastereoselectivity to give eight kinds of optically pure tetrahydrofuran core from a common α ‐oxyaldehyde. We also describe a comparison of the 1 H NMR, 13 C NMR, and CD spectral data of the eight isomers and give full details of the tetrahydrofuran‐ring construction including a model study of asymmetric alkynylation.