177607-70-4Relevant academic research and scientific papers
Synthesis and Absolute Configuration of Natural 2-Pyrones
Burkhardt, Immo,Dickschat, Jeroen S.
supporting information, p. 3144 - 3157 (2018/07/06)
2-Pyrones are frequently produced by microorganisms and often exhibit interesting bioactivities. Therefore, a short and easy synthetic access to these natural products is desirable. Synthetic routes to nectriapyrone, gibepyrone A, racemic gulypyrone A, (+)-germicidin C, (ent)-desoxygermicidin C and (ent)-prolipyrone A via a modular approach are presented, allowing the assignment of the absolute configurations of the latter three chiral compounds. The method failed for the synthesis of (ent)-phomapyrone B that was thus synthesized via a different route, resulting in an assignment of the absolute configuration of natural phomapyrone B.
A facile asymmetric synthesis of (S)-14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth
Zhang, Tao,Ma, Wei-Li,Li, Tian-Rui,Wu, Jia,Wang, Jun-Run,Du, Zhen-Ting
, p. 5201 - 5208 (2013/06/27)
An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth has been achieved. The target molecule was synthesized in six linear steps and in 30.3% overall yield from commercially available hexanoyl chloride, (S)-4-benzyloxazolidin-2-one and 1,9-nonanediol. The hexanoyl chloride was connected with (S)-4-benzyloxazolidin-2-one, and with the induction of the chiral oxazolidinone auxiliary, after chiral methylation, LAH reduction and then tosylation gave the chiral key intermediate 5 in high stereoselectivity. 1,9-Nonanediol, was selectively brominated, THP protected and subjected to Li2CuCl4-mediated C-C coupling to afford a C12 intermediate. The target molecule, (S)-14-methyl-1-octadecene, was obtained after the two parts were subjected to a second Li 2CuCl4-mediated C-C coupling. Our synthetic approach represents the first time a substrate-control asymmetric synthesis of (S)-14-methyl-1-octadecene has been reported.
Convergent enantioselective syntheses of two potential C25-C40 subunits of (-)-caylobolide A
De Joarder, Dripta,Jennings, Michael P.
scheme or table, p. 5124 - 5127 (2011/10/19)
The convergent syntheses of two possible diastereomers of the C25-C40 subunit resident in (-)-caylobolide A have been accomplished. The key reaction featured a chemoselective Ru-catalyzed cross-metathesis between a fully elaborated type I and two function
The first enantioselective synthesis of cytotoxic marine natural product palau'imide and assignment of its C-20 stereochemistry
Lan, Hong-Qiao,Ruan, Yuan-Ping,Huang, Pei-Qiang
supporting information; scheme or table, p. 5319 - 5321 (2010/09/03)
Methyl tetramate derivative 6 has been developed as a new building block for the flexible and racemization-free synthesis of methyl 5-benzyl-3- methyltetramate via alkylation, and used in the first asymmetric synthesis of palau'imide (1). This allowed the establishment of the hitherto unknown stereochemistry at the C-20 of palau'imide as S.
Total asymmetric synthesis of the potent immunosuppressive marine natural product microcolin A
Decicco, Carl P.,Grover, Paul
, p. 3534 - 3541 (2007/10/03)
The total asymmetric synthesis of the potent immunosuppressive compound microcolin A is reported. The synthesis establishes the absolute stereochemistry of microcolin A as C-36R, C-38R, and C-4S on the basis of the diastereoselective preparation of all four possible diastereomers of the lipid region (fragment A) and diastereoselective synthesis of fragment C starting from natural L-(S)-alanine. The strategy involves a convergent assemblage of three optically pure fragments and is amenable to chemical modifications to examine structural analogs for biological study.
