Total Synthesis of Eupomatilones 4 and 6: Structurally Rearranged and Atropisomerically Fluxional Lignan Natural Products
摘要:
A convergent and diastereocontrolled total synthesis of eupomatilones 4 and 6 is reported and was based on a diastereoselective hydroboration/oxidation sequence and a convergent Lipshutz biarylcuprate cross-coupling reaction. The structure of eupomatilone 6 is revised.
Asymmetric Total Synthesis of Dibenzocyclooctadiene Lignan Natural Products
作者:Robert S. Coleman、Srinivas Reddy Gurrala、Soumya Mitra、Amresh Raao
DOI:10.1021/jo051525i
日期:2005.10.1
Full details of the asymmetric total syntheses of the dibenzocyclooctadienelignans interiotherin A, angeloylgomisin R, gomisin O, and gomisin E (epigomisin O) are presented. The syntheses were based on a unified synthetic strategy involving a novel crotylation using the Leighton auxiliary that occurred with excellent asymmetric induction (>98:2 enantiomeric ratio), a diastereoselective hydroboration/Suzuki−Miyaura
?-Complexes of transition metals in organic synthesis. 9. Reactions of allyl organomanganese compounds with ?-bromine derivatives of esters of ?, ?-unsaturated carboxylic acids
作者:A. N. Kasatkin、O. Yu. Tsypyshev、T. Yu. Romanova、G. A. Tolstikov
DOI:10.1007/bf00957998
日期:1991.3
The allyl Mn(II) organic compounds R1CH = C(R2)CH2MnCl (R1 = H, Me; R2 = H, Me, Bu), obtained in situ from Grignard reagents and Li2MnCl4, react with esters of 4-bromocrotonic, (2-bromobutylidene)-, (4-bromo-2-butenylidene)-, (2-bromoisobutylidene)malonic, and (2-bromoheptylidene)cyanoacetic acids in THF at -78 to +20-degrees-C to give derivatives of substituted cyclopropanecarboxylic or cyclopropane-1,1-dicarboxylic acids. These derivatives contain a fragment of the allyl type. When ethers of 2-(bromomethyl)acrylic, 4-bromo-2-methyl-, and 4-bromo-3-methyl-2-butenoic acids are used, cross-combination products result.
Total Synthesis of the Eupomatilones
作者:Soumya Mitra、Srinivas Reddy Gurrala、Robert S. Coleman
DOI:10.1021/jo701415m
日期:2007.11.1
Full details of the total syntheses of five members of the eupomatilone family of lignans are reported.
KASATKIN, A. N.;TSYPYSHEV, O. YU.;ROMANOVA, T. YU.;TOLSTIKOV, G. A., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 656-663
作者:KASATKIN, A. N.、TSYPYSHEV, O. YU.、ROMANOVA, T. YU.、TOLSTIKOV, G. A.
DOI:——
日期:——
EL, IDRISSI MOSTAFA;SANTELLI, MAURICE, J. ORG. CHEM., 53,(1988) N 5, 1010-1016