TY - JOUR
T1 - Synthetic studies on zoapatanol
T2 - Construction of oxepanes via an intramolecular 1,3-dipolar cycloaddition strategy
AU - Shing, Tony K.M.
AU - Wong, Ching Hung
AU - Yip, Ting
N1 - Funding Information:
Acknowledgments: We thank the Hong Kong UPGC Direct Grant for financial support.
Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.
PY - 1996/5
Y1 - 1996/5
N2 - The nitrones derived from β-allyloxyaldehydes with a β-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a γ-allyloxyaldehyde with a γ-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose.
AB - The nitrones derived from β-allyloxyaldehydes with a β-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a γ-allyloxyaldehyde with a γ-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose.
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U2 - 10.1016/0957-4166(96)00149-8
DO - 10.1016/0957-4166(96)00149-8
M3 - Article
AN - SCOPUS:0029953154
VL - 7
SP - 1323
EP - 1340
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 5
ER -