- Stereoselective synthesis of tetrahydropyran-tetrahydrofuran (THP-THF) core of (+)-muconin via Prins cyclization
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A stereoselective synthesis of tetrahydropyran-tetrahydrofuran (THP-THF) core 2 of (+)-muconin (1) has been achieved using Prins cyclization as a key step to construct tetrahydropyran moiety. Other important transformations such as Wittig olefination, Sharpless epoxidation, regio-, and stereoselective exo-cyclization of the epoxy alcohol, titanocene induced regioselective deoxygenation of 2,3-epoxy alcohol, Grignard reaction, and Barton-McCombie reaction are successfully employed to accomplish the synthesis of THP-THF core 2.
- Yadav,Reddy, U.V. Subba,Reddy, B.V. Subba
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p. 3860 - 3863
(2014/07/08)
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- Conformational Diagnosis of Diethyl (4S,5S)-4,5-Bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate Based on the Stereochemical Outcomes of Representative Reactions As Compared with Those of Its 4,5-O-Isopropylidene Derivatives and on a Dichroic Exciton C
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In order to gain more insight into the conformation of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate (1) experimentally, some appropriate reactions of 1 and its derivative (S,S)-3, which bears isopropylidene protecting groups, ha
- Saito, Seiki,Narahara, Osamu,Ishikawa, Teruhiko,Asahara, Masahiro,Moriwake, Toshio,et al.
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p. 6292 - 6302
(2007/10/02)
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- SYNTHESIS OF AXIALLY DISSYMMETRIC 3,5-OCTADIENE FRAMEWORK WITH C2 CHIRALITY VIA PALLADIUM(II)-CATALYZED TWOFOLD SIGMATROPIC REARRANGEMENT
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Palladium(II)-catalyzed sigmatropic rearrangement of (4R,5R)-4,5-(bisacetoxy)-1,8-(bisbenzyloxy)-2(E),6(E)-octadiene has proceeded convergently to give (2S,7S)-2,7-(bisacetoxy)-1,8-(bisbenzyloxy)-3(E),5(E)-octadiene, translating the original chirality completely to the migration termini, which constitutes a novel synthesis of optically pure 3,5-octadiene with C2 chirality.
- Saito, Seiki,Hamano, Shin-ichi,Moriyama, Hiroshi,Okada, Keiji,Moriwake, Toshio
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p. 1157 - 1160
(2007/10/02)
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