Synthesis of Bishomoinositols and an Entry for Construction of a Substituted 3-Oxabicyclo[3.3.1]nonane Skeleton

Bekarlar, Merve
Aydin, Gokay
ŞAHİN, Ertan
Balcı, Metin
1,3,3a,7a-Tetrahydro-2-benzofuran was used as key compound for the synthesis of various bishomoinositol derivatives. The diene was subjected to an epoxidation reaction for further functionalization of the diene unit. The bisepoxide obtained was submitted to a ring-opening reaction with acid in the presence of water. Various bishomoinositols were synthesized. However, when the reaction was carried out in the presence of acetic anhydride, a substituted 3-oxabicyclo[3.3.1]nonane skeleton was formed. The mechanism of the formation of the products is discussed


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For the synthesis of various bishomo-inositol derivatives, 1,3,3a,7a-tetrahydro-2-benzofuran was used as the key compound. For further functionalization of the diene unit, the diene was subjected to photooxygenation, epoxidation, and cis-hydroxylation reactions. The endoperoxide linkage was cleaved by thiourea. The remaining double bond was subjected to epoxidation and cis-hydroxylation reactions. The epoxide rings and tetrahydrofuran rings formed were opened by acid-catalyzed reaction with sulfamic acid. T...
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An efficient synthesis of racemic and both enantiomeric forms of heteroaryl substituted gamma- and delta-lactone derivatives derived from allyl and homoallyl alcohol backbones has been accomplished via ring closing metathesis reaction. 2-Heteroaryl substituted allyl and homoallyl alcohols have been efficiently resolved through enzymatic method with high ee (97-99%) and known stereochemistry. Antimicrobial and antioxidant activities of target lactones were evaluated.
Synthesis and photooxygenation of homochiral 2-methylpyrrole derivatives of chiral amino alcohols: simple, selective access to chiral bicyclic lactams
Aydogan, F; Demir, Ayhan Sıtkı (2004-01-26)
Homochiral 2-methylpyrrole derivatives are synthesized in high yields starting from chiral amino alcohols and 5-chloro-3-pentene-2-one. The photooxygenation of these compounds in the presence of a photosynthesizer furnishes the pyrrolooxazolone structures in high diastereoselectivities. In all of the examples, trans-isomers are formed as the major products.
Citation Formats
A. BARAN, M. Bekarlar, G. Aydin, M. NEBİOĞLU, E. ŞAHİN, and M. Balcı, “Synthesis of Bishomoinositols and an Entry for Construction of a Substituted 3-Oxabicyclo[3.3.1]nonane Skeleton,” JOURNAL OF ORGANIC CHEMISTRY, pp. 1244–1250, 2012, Accessed: 00, 2020. [Online]. Available: