Journal
TETRAHEDRON
Volume 73, Issue 18, Pages 2705-2714Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.03.065
Keywords
Solanoeclepin A; SmI2-mediated radical ketyl cyclization; Cyclobutane formation; Tricyclo[5.2.1.0(1.6)]decene
Categories
Funding
- National Science Council
- National Tsing Hua University, Taiwan
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The construction of tricyclo[5.2.1.0(1.6)]decene skeleton was achieved by cyclobutane ring formation via improved radical reaction using SmI2-H2O-HFIP and SmI2-LiCl conditions in good yields. Those additives were studied to increase the reactivity of SmI2. Two interesting reactions via neighboring group participations are described for introducing the C4 oxygen functionality by the assistance of C6 substituent in a regioselective manner. (C) 2017 Elsevier Ltd. All rights reserved.
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