80374-37-4Relevant academic research and scientific papers
Sensing remote chirality: Stereochemical determination of β-, γ-, and δ-chiral carboxylic acids
Tanasova, Marina,Anyika, Mercy,Borhan, Babak
supporting information, p. 4274 - 4278 (2015/04/14)
Determining the absolute stereochemisty of small molecules bearing remote nonfunctionalizable stereocenters is a challenging task. Presented is a solution in which appropriately substituted bis(porphyrin) tweezers are used. Complexation of a suitably derivatized β-, γ-, or δ-chiral carboxylic acid to the tweezer induces a predictable helicity of the bis(porphyrin), which is detected as a bisignate Cotton Effect (ECCD). The sign of the ECCD curve is correlated with the absolute stereochemistry of the substrate based on the derived working mnemonics in a predictable manner.
Concise epoxide-based synthesis of the C14-C25 bafilomycin A1 polypropionate chain
Valentín, Elizabeth M.,Mulero, Marlenne,Prieto, José A.
supporting information; experimental part, p. 2199 - 2201 (2012/05/19)
An efficient nonaldol convergent synthesis of the C14-C25 polyketide fragment of bafilomycin A1 was completed in 16% overall yield and 8 steps in its longest linear sequence. This synthesis highlights the formation of the key fragments using a
REACTION OF DIANIONS DERIVED FROM β-KETOESTERS WITH EPOXIDES - UTILITY IN THE PREPARATION OF SYNTHETICALLY USEFUL TETRAHYDROFURANS.
Lygo, Barry,O'connor, Norval,Wilson, Peter R.
, p. 6881 - 6888 (2007/10/02)
Presented here are several examples which demonstrate that ether substituents α- or β- to an epoxide ring can be tolerated in the ring-opening reaction with β-keto ester dianions.Subsequent acid-promoted cyclisation of the γ-hydroxy β-ketoesters then leads to synthetically useful tetrahydrofurans, as demonstrated by application of this approach to the preparation of (+/-)-methyl nonactate and (+/-)-methyl 8-epi-nonactate.
SYNTHESIS OF THE ENANTIOMERIC FORMS OF CIS AND TRANS 1-BENZYLOXY-2,3-EPOXY BUTANE AND OF (3S,4S) 4-METHYL-3-HEPTANOL
Fuganti, Claudio,Grasselli, Piero,Servi, Stefano,Zirotti, Carlo
, p. 4269 - 4272 (2007/10/02)
The C4 erythro and threo diols (7) and (8) are converted either into the chiral epoxides (13) and (15) or into the enantiomers (14) and (16); the epoxide (13) is used as chiral synthon for the preparation of (3S,4S) 4-methyl-3-heptanol (21).
