123731-68-0Relevant articles and documents
Long-range stereo-relay: Relative and absolute configuration of 1,n-glycols from circular dichroism of liposomal porphyrin esters
MacMillan, John B.,Molinski, Tadeusz F.
, p. 9944 - 9945 (2004)
The relative and absolute configurations of long-chain syn- and anti-1,5-, 1,7- and 1,9-glycols were determined from exciton-coupled circular dichroism (ECCD) of the corresponding bis-5-(4′-carboxyl)-5,10,15,20-tetraphenylporphyrin esters measured in uniform (φ = 26 nm), unilamellar liposomes. Long-range transmission of configuration by ECCD is made possible through partial ordering of glycol ester-lipid molecules by liposomal bilayers. Copyright
A formal synthesis of porantheridine and an epimer
Bates, Roderick W.,Lu, Yongna
, p. 9460 - 9465 (2009)
(Chemical Equation Presented) A formal synthesis of porantheridine and a synthesis of its C6-epimer have been completed, employing silver-catalyzed allene cyclization to form a common cis-isoxazolidine intermediate and related N-acyl iminium ion intermediates for side-chain introduction. The stereochemistry of this step can be controlled by choice of the N-protection method.
Bioproduction of chiral epoxyalkanes using styrene monooxygenase from rhodococcus sp. ST-10 (RhSMO)
Toda, Hiroshi,Imae, Ryouta,Itoh, Nobuya
, p. 3443 - 3450 (2015/02/05)
We describe the enantioselective epoxidation of straight-chain aliphatic alkenes using a biocatalytic system containing styrene monooxygenase from Rhodococcus sp. ST-10 and alcohol dehydrogenase from Leifsonia sp. S749. The biocatalyzed enantiomeric epoxidation of 1-hexene to (S)-1,2-epoxyhexane (44.6 mM) using 2-propanol as the hydrogen donor was achieved under optimized conditions. The biocatalyst had broad substrate specificity for various aliphatic alkenes, including terminal, internal, unfunctionalized, and di- and tri-substituted alkenes. Here, we demonstrate that this biocatalytic system is suitable for the efficient production of enantioenriched (S)-epoxyalkanes.
Total synthesis of neopeltolide and analogs
Cui, Yubo,Tu, Wangyang,Floreancig, Paul E.
scheme or table, p. 4867 - 4873 (2010/08/06)
Neopeltolide, a potent cytotoxin from a Carribean sponge, was synthesized through a brief sequence that highlights the use of ethers as oxocarbenium ion precursors. Other key steps include an acid-mediated etherification and sequence that features a Sonogashira reaction, an intramolecular alkyne hydrosilylation reaction, and a Tamao oxidation. The alkene that is required for the oxidative cyclization can be hydrogenated to provide access to the natural product or an epimer, or can be epoxidized or dihydroxylated to form polar analogs.