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Short Paper | Regular issue | Vol 96, No. 3, 2018, pp.453-460
Published online, 7th February, 2018
DOI: 10.3987/COM-17-13776
Prins Reaction Using Trioxane for Trisubstituted, cis-Fused Hexahydro-2H-furo[3,2-b]pyran Derivative

Oriel Hlokoane, Hiyori Itagaki, Manami Chiba, Taiki Noda, Yuichi Takasaki, Kei Miyako, Ryuichi Sakai, Yuichi Ishikawa,* and Masato Oikawa*

*Graduate School of Nanobioscience, Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan

Abstract

The construction of cis-fused heterobicyclic system involved in neuroactive natural products such as dysiherbaine has been accomplished by employing Prins strategy using 1,3,5–trioxane as an equivalent for formaldehyde. The reactions allowed stereoselective construction of the trisubstituted cis-fused hexahydro-2H-furo[3,2-b]pyran with maximum yield of 60%.