Selective Formation of trans/threo/cis and cis/threo/cis Bis-Tetrahydrofurans from the Same Diene Diols

Fujioka, Hiromichi; Oki, Tomohiro; Hayashi, Tatsuya; Yamakawa, Maki; Kurachi, Takeshi; Nakahara, Kenji; Maehata, Ryota; Hamada, Tomohito; Murai, Kenichi; Kita, Yasuyuki

doi:10.3987/com-13-s(s)102

Cited by 2 publications

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“…In this manuscript, we report the stereoselective synthesis of a fused -bis THF skeleton by the double haloetherification of a diene diol substrate and a related derivative, as part of our ongoing research toward the stereoselective synthesis of bioactive natural products containing a 2,5-disubstituted bis -THF ring, and the highly stereoselective formation of trans / trans and cis / cis fused -bis THF compounds in high yields using a one-pot procedure (Scheme ).…”

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confidence: 99%

Stereoselective Construction of 2,7-Disubstituted fused-Bis Tetrahydrofuran Skeletons: Biomimetic-Type Synthesis and Biological Evaluation of (±)- and (−)-Aplysiallene and Their Derivatives

et al. 2015

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A series of trans/trans and cis/cis fused-bis tetrahydrofuran compounds have been obtained stereoselectively in high yields via a one-pot operation involving the intramolecular haloetherification of (Z,Z)-diene diol 19a and (E,E)-diene disilylether 19d, respectively. This method was subsequently applied to the biomimetic-type synthesis of (±)- and (-)-aplysiallene. The inhibitory activities of these compounds and their bromodiene isomers toward Na(+)/K(+) ATPase were determined in vitro, and gave IC50 values of approximately 15 μM in all cases.

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Section: Introductionmentioning

confidence: 99%

Stereoselective Construction of 2,7-Disubstituted fused-Bis Tetrahydrofuran Skeletons: Biomimetic-Type Synthesis and Biological Evaluation of (±)- and (−)-Aplysiallene and Their Derivatives

et al. 2015

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ChemInform Abstract: Selective Formation of trans/threo/cis and cis/threo/cis Bis‐tetrahydrofurans from the Same Diene Diols.

et al. 2014

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Selective Formation of trans/threo/cis and cis/threo/cis Bis-tetrahydrofurans from the Same Diene Diols. -(FUJIOKA*, H.; OKI, T.; HAYASHI, T.; YAMAKAWA, M.; KURACHI, T.; NAKAHARA, K.; MAEHATA, R.; HAMADA, T.; MURAI, K.; KITA, Y.; Heterocycles 88 (2014) 2, Special Issue, 1323-1336, http://dx.doi.org/10.3987/COM-13-S(S)102 ; Grad. Sch. Pharm. Sci., Osaka Univ., Suita, Osaka 565-0871, Japan; Eng.) -R. Staver 23-124

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Selective Formation of trans/threo/cis and cis/threo/cis Bis-Tetrahydrofurans from the Same Diene Diols

Cited by 2 publications

References 12 publications

Stereoselective Construction of 2,7-Disubstituted fused-Bis Tetrahydrofuran Skeletons: Biomimetic-Type Synthesis and Biological Evaluation of (±)- and (−)-Aplysiallene and Their Derivatives

Stereoselective Construction of 2,7-Disubstituted fused-Bis Tetrahydrofuran Skeletons: Biomimetic-Type Synthesis and Biological Evaluation of (±)- and (−)-Aplysiallene and Their Derivatives

ChemInform Abstract: Selective Formation of trans/threo/cis and cis/threo/cis Bis‐tetrahydrofurans from the Same Diene Diols.

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