- Stereoselective Total Synthesis of Polyether Ionophore Antibiotics, Isolasalocid A and Lasalocid A. Part 2. The Total Synthesis via Stereoselective Construction of the B Rings by Chelation-Controlled Cyclization under Thermodynamic Conditions
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Stereoselective total synthesis of isolasalocid A (1) and lasalocid A (2) was achieved via construction of the tetrahydrofuran rings by chelation-controlled cyclization of the corresponding p-methoxyphenyl substituted allyl alcohols (6, 7) under thermodyn
- Horita, Kiyoshi,Noda, Ichio,Tanaka, Kazuhiro,Oikawa, Yuji,Yonemitsu, Osamu
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p. 5997 - 6018
(2007/10/02)
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- Stereoselective synthesis of polyether antibiotics, lasalocid A and isolasalocid A, via a chelation-controlled formation of tetrahydrofuran rings under thermodynamic conditions
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The B-rings (2,5-trans-tetrahydrofurans) of lasalocid A (6) and isolasalocid A (7) were stereoselectively constructed from the corresponding p-methoxyphenylallyl alcohols (13a, 13b) by treatment with ZnBr2 to give C13-C24 fragments (14a, 14b) via a new chelation-controlled cyclization under thermodynamic conditions. After their conversion into lasalocid ketone (19) and BOM-isolasalocid ketone (20), coupling with the C1-C11 aldehyde (22) completed the synthesis of 6 and 7, respectively.
- Noda,Horita,Oikawa,Yonemitsu
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p. 6035 - 6038
(2007/10/02)
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