Abstract
Thietanes are important aliphatic four-membered thiaheterocycles that are found in the pharmaceutical core and structural motifs of some biological compounds. They are also useful intermediates in organic synthesis. Various synthetic methods of thietanes have been developed, including inter- and intramolecular nucleophilic thioetherifications, photochemical [2 + 2] cycloadditions, ring expansions and contractions, nucleophilic cyclizations, and some miscellaneous methods. The recently developed methods provide some new strategies for the efficient preparation of thietanes and their derivatives. This review focuses on the synthetic methods to construct thietane backbones developed during 1966 to 2019.
Highlights
Thietanes are a class of important aliphatic four-membered thiaheterocycles
Inter- and intramolecular photochemical [2 + 2] cycloadditions of alkenes and thiocarbonyl compounds are another important route for the synthesis of thietanes [15,16], especially, spirothietanes [17,18]
In 2007, Nishizono and co-workers used 2,2-bis(bromomethyl)propane-1,3-diol (11) as starting material to prepare thietanose nucleosides 2 and 14. They first carried out a double displacement with sodium sulfide to obtain thietane-3,3diyldimethanol (13), which was further converted into two different thietanose nucleosides 2 and 14 [33] (Scheme 2)
Summary
Thietanes are a class of important aliphatic four-membered thiaheterocycles. Inter- and intramolecular photochemical [2 + 2] cycloadditions (thia-Paternò–Büchi reactions) of alkenes and thiocarbonyl compounds are another important route for the synthesis of thietanes [15,16], especially, spirothietanes [17,18]. The ring-contractions of five and six-membered aliphatic thiaheterocycles have been seldom applied in the preparation of thiatetraoses [20,21]. Both nucleophilic and electrophilic ring expansions of thiiranes have been developed to synthesize thietanes [22,23]. A special focus is on the construction of the thietane ring, excluding methods for the simple modifications of the thietane rings and their side chains [26,27,28,29,30,31]
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