113548-13-3Relevant articles and documents
Efficient and stereoselective dimerization of pyrroloindolizine derivatives inspired by a hypothesis for the biosynthesis of complex myrmicarin alkaloids
Movassaghi, Mohammad,Ondrus, Alison E.,Chen, Bin
, p. 10065 - 10074 (2007)
(Chemical Equation Presented) Pyrroloindolizine derivatives participate in efficient and stereoselective homo- and heterodimerization reactions upon treatment with Bronsted or Lewis acids. The distinctive ability of pyrroloindolizines to act as azafulvenium ion precursors provides direct access to both heptacyclic and hexacyclic dimeric products. The inherent reactivity of these structures suggests a concise synthesis of complex myrmicarin alkaloids, via dimerization of pyrroloindolizines, and may have implications for the biosynthesis of these intriguing alkaloids.
A practical synthesis of long-chain iso-fatty acids (iso-C 12-C19) and related natural products
Richardson, Mark B.,Williams, Spencer J.
, p. 1807 - 1812 (2013)
A gram-scale synthesis of terminally-branched iso-fatty acids (iso-C 12-C19) was developed commencing with methyl undec-10-enoate (methyl undecylenate) (for iso-C12-C14) or the C15 and C16 lactones pentadecanolide (for iso-C 15-C17) and hexadecanolide (for iso-C18-C 19). Central to the approaches outlined is the two-step construction of the terminal isopropyl group through addition of methylmagnesium bromide to the ester/lactones and selective reduction of the resulting tertiary alcohols. Thus, the C12, C17 and C18 iso-fatty acids were obtained in three steps from commercially-available starting materials, and the remaining C13-C16 and C19 iso-fatty acids were prepared by homologation or recursive dehomologations of these fatty acids or through intercepting appropriate intermediates. Highlighting the synthetic potential of the iso-fatty acids and various intermediates prepared herein, we describe the synthesis of the natural products (S)-2,15-dimethylpalmitic acid, (S)-2-hydroxy-15-methylpalmitic acid, and 2-oxo-14-methylpentadecane.
Synthesis of enantioenriched α-chiral bicyclo[1.1.1]pentanes
Wong, Marie L. J.,Mousseau, James J.,Mansfield, Steven J.,Anderson, Edward A.
supporting information, p. 2408 - 2411 (2019/03/26)
Bicyclo[1.1.1]pentanes (BCPs), useful surrogates for para-substituted arenes, alkynes, and tert-butyl groups in medicinal chemistry, are challenging to prepare when featuring stereogenic centers adjacent to the BCP. We report the development of an efficie
Stereoselective Synthesis of a Highly Oxygenated δ-Lactone Related to the Core Structure of (-)-Enterocin
Wegmann, Marcus,Bach, Thorsten
supporting information, p. 209 - 217 (2016/12/24)
The title compound was prepared in a concise route starting from an appropriately protected (S)-glyceraldehyde. A highly diastereoselective (d.r. >95:5) Mukaiyama aldol reaction of an acetoacetate-derived silyl enol ether served as the initial step of the synthetic sequence. It was found that protection of the glyceraldehyde as a butane-2,3-dione acetal is required to achieve the desired diastereoselectivity. Upon lactonization, a Tsuji-Trost allylation and a subsequent one-pot reaction cascade including an ozonolysis and an α-hydroxylation gave diastereoselective access to the desired α-hydroxy-β-oxo-δ-lactone. Alternative synthetic approaches are discussed and proof for the configuration of the product is presented.
