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Intramolecular Parallel [4+3] Cycloadditions of Cyclopropane 1,1‐Diesters with [3]Dendralenes: Efficient Construction of [5.3.0]Decane and Corresponding Polycyclic Skeletons
Author(s) -
Zhang Chi,
Tian Jun,
Ren Jun,
Wang Zhongwen
Publication year - 2017
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.201605190
Subject(s) - intramolecular force , cycloaddition , cyclopropane , decane , octane , chemistry , ring (chemistry) , stereochemistry , computational chemistry , combinatorial chemistry , organic chemistry , catalysis
Abstract Aiming to develop efficient and general strategies for construction of complex and diverse polycyclic skeletons, we have successfully developed [4+3]IMPC (intramolecular parallel cycloaddition) of cyclopropane 1,1‐diesters with [3]dendralenes. With a combination of the [4+3]IMPC and subsequent [4+ n ] cycloadditions, trans ‐[5.3.0]decane skeleton and its corresponding structurally complex and diverse polycyclic variants could be constructed efficiently. This novel [4+3] cycloaddition reaction mode of donor–acceptor cyclopropanes proceeds as a result of the ring‐strain relief of a trans ‐[3.3.0]octane. We strongly believe that the developed methods will demonstrate potential applications in natural products synthesis and drug discovery.