176900-63-3Relevant academic research and scientific papers
Enzymatic synthesis of (2E,4E)-(6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one, the sex pheromone of Matsucoccus matsumurae Japanese pine bast scale
Lin, Guo-Qiang,Xu, Wei-Chu
, p. 375 - 380 (1996)
The sex pheromone of Matsucoccus matsumurae Japanese pine bast scale (2E,4E)-(6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one (1) was synthesized with stereocontrol from (2R,4S)-5-acetoxy-2,4-dimethyl-pentanol (3), which in turn was prepared by lipase-catalyzed transesterification of meso-2,4-dimethyl-1,5-propanediol (2).
Synthesis of hydroxyphthioceranic acid using a traceless lithiation-borylation-protodeboronation strategy
Rasappan, Ramesh,Aggarwal, Varinder K.
, p. 810 - 814 (2014/11/08)
In planning organic syntheses, disconnections are most often made adjacent to functional groups, which assist in C-C bond formation. For molecules devoid of obvious functional groups this approach presents a problem, and so functionalities must be installed temporarily and then removed. Here we present a traceless strategy for organic synthesis that uses a boronic ester as such a group in a one-pot lithiation-borylation-protodeboronation sequence. To realize this strategy, we developed a methodology for the protodeboronation of alkyl pinacol boronic esters that involves the formation of a boronate complex with a nucleophile followed by oxidation with Mn(OAc) 3 in the presence of the hydrogen-atom donor 4-tert-butylcatechol. Iterative lithiation-borylation- protodeboronation allows the coupling of smaller fragments to build-up long alkyl chains. We employed this strategy in the synthesis of hydroxyphthioceranic acid, a key component of the cell-wall lipid of the virulent Mycobacterium tuberculosis, in just 14 steps (longest linear sequence) with full stereocontrol.
Chemoenzymatic approach to the total synthesis of (+)-bourgeanic acid
Yadav, Jhillu S.,Rao, Tenneti Srinivasa,Yadav, Nagendra Nath,Rao, Kovvuru V. Raghavendra,Reddy, Basi V. Subba,Al Khazim Al Ghamdi, Ahmad
experimental part, p. 788 - 792 (2012/04/04)
A highly stereoselective total synthesis of (+)-bourgeanic acid has been accomplished by an enzymatic desymmetrization approach to create two methyl chiral centers. Other key steps involved in this approach are a Wittig reaction, a Gilman reaction, and TE
Synthesis of the alkaloid tyroscherin by an aldol/Curtius strategy
Ugele, Markus,Maier, Martin E.
supporting information; experimental part, p. 2633 - 2641 (2010/05/01)
The alkaloid tyroscherin (2), which contains a vicinal anti-amino alcohol subunit was prepared from 4-hydroxyphenylpropionic acid (5) and meso-diol 9. After desymmetrization of diol 9 and suitable protecting group manipulations, one terminus was extended via a Claisen rearrangement giving rise to enoate ent-15. The missing carbon on the other end could be incorporated using MeMgCl/CuBr·SMe2 leading eventually to aldehyde ent-22. The acylated oxazolidinone 32 derived from acid 5 and aldehyde ent-22 were combined in an aldol reaction. A subsequent Curtius rearrangement on the carboxylic group furnished the amino function of tyroscherin (2). In a proof of concept study the same strategy was used to prepare tyroscherin analog 28.
Total synthesis and structural assignment of spongidepsin through a stereodivergent ring-closing-metathesis strategy
Chen, Jiehao,Forsyth, Craig J.
, p. 2148 - 2152 (2007/10/03)
Eight diastereomeric probes (1) were generated to synthesize the novel, anti-proliferative marine natural product spongidepsin (2) and to determine its absolute stereochemistry. A key step was the formation of the macrocycle by ring-closing metathesis.
Assignment of absolute stereochemistry and total synthesis of (-)-spongidepsin
Ghosh, Arun K.,Xu, Xiaoming
, p. 2055 - 2058 (2007/10/03)
Equation presented. An enantioselective total synthesis of (-)-spongidepsin (2) and elucidation of the absolute stereochemistry of its four stereocenters are described. Spongidepsin (2), a 13-membered depsipeptide isolated from the Vanuatu marine sponge S
An improved synthesis of the scyphostatin side-chain
McAllister, Graeme D.,Taylor, Richard J. K.
, p. 2551 - 2554 (2007/10/03)
A formal synthesis of the lipophilic side-chain of scyphostatin has been achieved using a convergent synthesis, in 16% yield over six steps. This synthesis involves enzymatic desymmetrisation of a meso-diol, resolution of 2-methylbutan-1-ol, stereoselective hydrozirconation of a volatile acetylene and a Negishi-style cross coupling.
Synthesis (and alternative proof of configuration) of the scyphostatin C(1')-C(20') trienoyl fragment.
Hoye,Tennakoon
, p. 1481 - 1483 (2007/10/03)
[reaction--see text] Each of four diastereomers of structure 2, corresponding to the lipophilic side chain of scyphostatin (1), were prepared. Careful analysis of their NMR spectral data and comparison with those of the natural product corroborates the re
