503620-04-0Relevant academic research and scientific papers
New synthesis of syn-stereodiad building block for polyketides. Formal synthesis of arenamides A and C
Shklyaruck
, p. 582 - 590 (2015)
Abstract An efficient procedure has been developed for the transformation of (7S)-7-(3-bromoprop-1-en-2-yl)-5,5-dimethyl-4,6-dioxaspiro[2.5]octane [available from diethyl (S)-malate] into methyl 2-[(4S)-2,2-dimethyl-5-methylidene-1,3-dioxan-4-yl]acetate,
Synthesis of the C-8-C-24 Fragment of Maltepolide C by Using a Tandem Dihydroxylation/SN2 Cyclization Sequence
Mohapatra, Debendra K.,Reddy, D. Sai,Reddy, G. Sudhakar,Yadav, Jhillu S.
, p. 5266 - 5274 (2015/08/18)
A highly stereoselective synthesis of the C-8-C-24 fragment of maltepolide C has been achieved in a convergent and efficient manner by utilizing a tandem Sharpless asymmetric dihydroxylation (SAD)/SN2 cyclization reaction sequence as the key st
Novel iodine catalyzed diastereoselective synthesis of trans-2,6- disubstituted tetrahydro-2H-pyrans: Synthesis of C1-C13 fragment of bistramide-A
Yadav, Jhillu Singh,Gyanchander, Eppa,Mishra, Anand Kumar,Adithya, Peddapuram,Das, Saibal
, p. 5879 - 5882 (2013/10/21)
A new method for the stereoselective synthesis of trans 2.6-disubstituted tetrahydro-2H-pyrans has been developed involving iodine catalyzed allylation of tetrahydro-2H-pyranol with excellent trans selectivity. The method was also applied toward the construction of C1-C13 fragment of bistramide-A in 11 steps with 21.4% overall yield.
Synthesis of bioactive natural products by asymmetric syn-and anti-aldol reactions
Ghosh, Arun K.,Dawson, Zachary L.
body text, p. 2992 - 3002 (2010/04/02)
The use of several variants of the asymmetric aldol reaction as key steps in the syntheses of bioactive target molecules is described. Georg Thieme Verlag Stuttgart.
Total synthesis of arenamide A and its diastereomer
Chandrasekhar,Pavankumarreddy,Sathish
scheme or table, p. 6851 - 6854 (2010/05/03)
Arenamide A and its diastereomer have been synthesized in a convergent fashion. The key steps involved in this synthesis are Sharpless asymmetric epoxidation, C-C bond formation, and macrolactamization.
Total synthesis of (-)-ulapualide A, a novel tris-oxazole macrolide from marine nudibranchs, based on some biosynthesis speculation
Pattenden, Gerald,Ashweek, Neil J.,Baker-Glenn, Charles A. G.,Kempson, James,Walker, Gary M.,Yee, James G. K.
supporting information; experimental part, p. 1478 - 1497 (2008/10/09)
A new, second generation, total synthesis of ulapualide A (1), whose stereochemistry was recently determined from X-ray analysis of its complex with the protein actin, is described. The synthesis is designed and based on some speculation of the biosynthet
Total synthesis of (-)-ulapualide A: The danger of overdependence on NMR spectroscopy in assignment of stereochemistry
Pattenden, Gerald,Ashweek, Neil J.,Baker-Glenn, Charles A. G.,Walker, Gary M.,Yee, James G. K.
, p. 4359 - 4363 (2008/03/12)
Lessons learnt: The asymmetric total synthesis of the macrolide (-)-ulapualide A has been accomplished. Interestingly, the 1H NMR spectrum and chiroptical data of the macrolide and of a previously synthesized diastereoisomer with opposite stere
A Baylis-Hillman approach to the synthesis of C1-C11 fragment of caribenolide I
Seck, Matar,Franck, Xavier,Seon-Meniel, Blandine,Hocquemiller, Reynald,Figadère, Bruno
, p. 4175 - 4180 (2007/10/03)
Stereoselective synthesis of C1-C11 fragment of caribenolide I, a potent antitumour macrolide isolated from a marine dinoflagellate Amphidinium sp. is described. The key steps rely on asymmetric aldol reactions, to control the absolu
Enantioselective total synthesis of (+)-amphidinolide T1
Ghosh, Arun K.,Liu, Chunfeng
, p. 2374 - 2375 (2007/10/03)
An enantioselective first total syntheis of amphidinolide T1 (1) is described. Amphidinolide T1 (1), a 19-membered macrolide isolated from Amphidinium sp., has shown potent antitumor properties against a variety of NCI tumor cell lines. The synthesis is convergent and involves the assembly of C1-C10 segment 2 and C11-C21 segment 3 by an oxocarbenium ion-mediated alkylation and Yamaguchi macrolactonization sequence. The synthesis of fragment 2 involves an efficient cross metathesis and hydrogenation sequence between the terminal olefins of 5 and 6 to form the C4-C5 carbon-carbon bond. Enol ether 4 is designed to be the surrogate of fragment 3 where the sensitive C16-exo-methylene and the C13-hydroxyl group were protected as the bromoether derivative during the Lewis acid-catalyzed alkylation process. Both stereocenters in fragment 5 as well as the C2 and C3 stereocenters in fragment 4 are accessed by a highly diastereoselective ester-derived titanium enolate-mediated syn-aldol reaction. The bromoether derivative 24 was unraveled at the final stage of the synthesis, providing (+)-amphidinolide T1. Copyright
