147973-69-1Relevant academic research and scientific papers
Synthesis of Decytospolide A, B and Their C-3 Epimers Using Stereoselective Oxypalladation
Kurogome, Yuji,Hattori, Yasunao,Makabe, Hidefumi
, p. 765 - 771 (2016)
Stereoselective synthesis of decytospolide A and B and their C-3 epimers, which have a 2,6-cis-tetrahydropyran ring, has been achieved in high stereoselectivity and yield. The oxypalladation of single diastereomers of 6-(benzyloxy)-7-hydroxydodec-2-enyl 2
Formal and total syntheses of herbarumin i and II, respectively from (R)-2,3-cyclohexylideneglyceraldehyde
Goswami, Dibakar,Chattopadhyay, Angshuman
experimental part, p. 764 - 768 (2012/09/05)
Vinyl Grignard addition to 2, obtained via a nitroaldol reaction of (R)-2,3-cyclohexylideneglyceraldehyde 1, afforded 3 with absolute stereoselectivity. This was transformed into 7, a known intermediate for the formal synthesis of herbarumin I A. Condensation of 7 with 10, another intermediate obtained from 1 afforded 11. The RCM reaction of 11 in the presence of Grubbs second generation catalyst Ru II and global debenzylation of the product in the presence of TiCl4 furnished B. The efficacy of the entire route was due to its operational simplicity, the easy accessibility of 1, all of the reactions being inexpensive and the high stereoselectivity of the asymmetric C-C bond forming reactions involved, as well as E-selectivity of the RCM reaction.
Applications of remote stereocontrol using allylstannanes: An approach to the stereoselective synthesis of aliphatic polyols
McNeill, Alan H.,Thomas, Eric J.
experimental part, p. 257 - 266 (2011/02/27)
(4R,2E)-4-Benzyloxy-octa-2,7-dienyl(tributyl)stannane was transmetalated by tin(IV) chloride to generate an allyltin trichloride, which reacted with aldehydes to give (3Z)-1,5-syn-5-benzyloxynona-3,8-dien-1-ols with useful 1,5-stereocontrol. O-Benzylation, hydroboration and oxidation of the terminal double-bond of the product from 2-methylpropanal gave (5R,9S,6Z)-5,9- dibenzyloxy-10-methylundec-6-enal. Further reactions with 4-alkoxyalk-2- enylstannanes proceeded with useful 1,5-stereocontrol to give open-chain products with hydroxy or benzyloxy substituents stereoselectively disposed at remote positions along the chain.
Enantioselective synthesis of α-benzyloxy-ω-alkenals: application to the synthesis of (+)-exo-brevicomin, (+)-iso-exo-brevicomin, and (-)-isolaurepan
Prasad, Kavirayani R.,Anbarasan, Pazhamalai
, p. 1419 - 1427 (2008/02/11)
The enantioselective synthesis of α-benzyloxy aldehydes containing a terminal alkene was carried out from chiral pool l-(+)-tartaric acid by employing the stereoselective reduction of a 1,4-diketone as the key step. The synthetic utility of these aldehyde
Asymmetric synthesis of unsaturated α-benzyloxyaldehydes: An enantioselective synthesis of (+)-exo-brevicomin
Prasad, Kavirayani R.,Anbarasan, Pazhamalai
, p. 3951 - 3953 (2007/10/03)
Enantioselective synthesis of α-hydroxy aldehydes with an alkene tether was accomplished from l-(+)-tartaric acid, employing stereoselective reduction of a 1,4-diketone with L-selectride as the key step. Synthetic utility of these aldehydes was demonstrat
A new access to enantiopure β-hydroxylated piperidines from N-Boc-2- acyloxazolidines. Application to the synthesis of (-)-desoxoprosopinine and (+)-pseudoconhydrine
Agami, Claude,Couty, Francois,Lam, Hubert,Mathieu, Helene
, p. 8783 - 8796 (2007/10/03)
The synthesis of (-)-desoxoprosopinine and (+)-pseudoconhydrine were achieved from a common oxazolidine precursor. The three stereocenters present in (-)-desoxoprosopinine as well as the two stereocenters of (+)- pseudoconhydrine were created in highly stereoselective ways. The stereoselectivity observed during the reduction of the ketone moiety in the starting oxazolidine was dependent on the occurrence of a chelated intermediate. The others stereocenters arose from stereoselective reductions or alkylations of intermediate iminium ions.
Stereoselective Synthesis of Aliphatic 1,5,9,13-Polyols using (δ-Alkoxyallyl)stannanes
McNeill, Alan H.,Thomas, Eric J.
, p. 1669 - 1672 (2007/10/02)
Treatment of aliphatic aldehydes with the allyltin trichloride generated from the 4-benzyloxyocta-2,7-dienylstannane 18 and tin(IV)chloride provides stereoselective access to polyhydroxylated compounds with the hydroxyl groups at positions 1,5,9,13- etc.
