Conversion of 2-Heptenolides into Substituted Oxocene Systems. Its Application to the Synthesis of (+)-Lauthisan
作者： Kazunori Tsushima , Akio Murai
DOI: 10.1246/CL.1990.761
关键词: Trifluoromethanesulfonate 、 Chemistry 、 Lithium 、 Organic chemistry 、 General chemistry
摘要: 2-Heptenolide was smoothly transformed into the α,β,γ,δ-dienol triflate, which reacted with lithium dialkylcuprates to afford α-alkylated oxocenes in good yields. The methodology applied effectively synthesis of (+)-lauthisan.
csj.jp参考文章(8)
Kōichi Mikami, Naoyuki Kishi, Takeshi Nakai, Yoshiji Fujita, New sigmatropic sequences based on the [2,3]-wittig rearrangement of the bis-allylic ether system : A general approach to regiocontrolled c—c bond formation of allylic moieties leading to unsaturated carbonyl compounds Tetrahedron. ,vol. 42, pp. 2911- 2918 ,(1986) , 10.1016/S0040-4020(01)90580-0
Dieter Enders, Herbert Eichenauer, Asymmetrische Synthesen via metallierte chirale Hydrazone. Enantioselektive Alkylierung von cyclischen Ketonen und Aldehyden1 Chemische Berichte. ,vol. 112, pp. 2933- 2960 ,(1979) , 10.1002/CBER.19791120820
J.Stephen Clark, Andrew B. Holmes, A strategy for the asymmetric synthesis of medium ring oxygen heterocycles: Enantioselective total synthesis of (+)-octahydrodeacetyldebromolaurencin Tetrahedron Letters. ,vol. 29, pp. 4333- 4336 ,(1988) , 10.1016/S0040-4039(00)80490-6
Hiyoshizo Kotsuki, Yasuyuki Ushio, Isao Kadota, Masamitsu Ochi, Stereoselective reduction of bicyclic ketals. A new, enantioselective synthesis of isolaurepinnacin and lauthisan skeletons Journal of Organic Chemistry. ,vol. 54, pp. 5153- 5161 ,(1989) , 10.1021/JO00282A037
Akio Fukuzawa, Tadashi Masamune, Laurepinnacin and isolaurepinnacin, new acetylenic cyclic ethers from the marine red alga laurencia pinnata yamada Tetrahedron Letters. ,vol. 22, pp. 4081- 4084 ,(1981) , 10.1016/S0040-4039(01)82070-0
Tadashi Masamune, Hajime Matsue, Hisashi Murase, Synthetic Studies of Laurencin and Related Compounds. IV. Synthesis ofcis-2-Ethyl-8-formyl-3,4,7,8-dihydro-2H-oxocin-3-one 3-Ethylene Acetal and Related Compounds Bulletin of the Chemical Society of Japan. ,vol. 52, pp. 127- 134 ,(1979) , 10.1246/BCSJ.52.127
Tadashi Masamune, Hisashi Murase, Hajime Matsue, Akio Murai, Synthetic Studies of Laurencin and Related Compounds. V. Transformation ofcis-2-Ethyl-8-formyl-3,4,7,8-dihydro-2H-oxocin-3-one 3-Ethylene Acetal into (±)-Laurencin Bulletin of the Chemical Society of Japan. ,vol. 52, pp. 135- 141 ,(1979) , 10.1246/BCSJ.52.135
Larry E. Overman, Andrew S. Thompson, Total synthesis of (-)-laurenyne. Use of acetal-initiated cyclizations to prepare functionalized eight-membered cyclic ethers Journal of the American Chemical Society. ,vol. 110, pp. 2248- 2256 ,(1988) , 10.1021/JA00215A040