51268-87-2Relevant articles and documents
Stereoselective synthesis of (3R,6S)-6-hydroxylasiodiplodin
Bujaranipalli, Sheshurao,Das, Saibal
supporting information, p. 1653 - 1655 (2016/04/04)
The first stereoselective synthesis of polyketide natural product (3R,6S)-6-hydroxylasiodiplodin (1) has been described starting from commonly available starting materials d-mannitol and 2,4,6-trihydroxybenzoic acid. The key reactions involved are Keck asymmetric allylation, Stille coupling, De Brabander's esterification, and ring-closing metathesis (RCM) reaction. The total synthesis was achieved in 19.3% overall yield making the route significant.
Stereoselective total synthesis of cananginones (D-I) using Ireland-Claisen rearrangement as a key step
Kuilya, Tapan Kumar,Chatterjee, Shamba,Goswami, Rajib Kumar
, p. 2905 - 2918 (2014/04/17)
A strategy for stereoselective total synthesis of α-substituted γ-hydroxymethyl γ-butyrolactone containing bioactive natural products cananginones (D-I) has been developed using cheap and commercially available d-mannitol as a chiral pool. The Ireland-Cla
Total synthesis of diastereomeric marine butenolides possessing a syn-aldol subunit at C10 and C11 and the related C11-ketone
Wang, Yan,Dai, Wei-Min
supporting information; scheme or table, p. 187 - 196 (2010/03/04)
Two diastereomeric marine butenolides, (4S,10R,11R)- and (4S,10S,11S)-4,11-dihydroxy-10-methyldodec-2-en-1,4-olide, possessing a syn-aldol subunit at C10 and C11 have been efficiently synthesized by using a three-module coupling strategy. The enantiomeric syn-aldol modules prepared by the syn-selective aldol reaction of the norephedrine-derived chiral propionates were coupled with the chiral C3-C7 module via 1,3-dithiane bisalkylation. The butenolide ring was then installed via a high-yielding ring-closing metathesis (RCM) reaction. Oxidation of the diastereomeric C11-alcohols furnished the corresponding C11-ketones, which are produced by the same marine microorganism.
Total synthesis of nonenolide
Meshram, Harshadas Mitaram,Kumar, Dachepally Aravind,Ramesh, Palakuri
scheme or table, p. 1422 - 1427 (2010/09/12)
A novel synthetic route has been reported for the synthesis of nonenolide. The syntheses of fragments were initiated from commercially available and inexpensive starting materials. The synthesis involves key steps like Sharpless epoxidation, Jacobsen's re
The formal synthesis of isofebrifugine using stereoselective intramolecular Michael addition
Sudhakar, Neela,Srinivasulu, Gannoju,Rao, Ganipisetti Srinivas,Rao, Batchu Venkateswara
experimental part, p. 2153 - 2158 (2009/04/05)
The formal synthesis of isofebrifugine, a bioactive alkaloid, was achieved via a stereoselective intramolecular Michael addition reaction from d-mannitol.
Asymmetric total synthesis of martinelline and martinellic acid
Ikeda, Shuhei,Shibuya, Masatoshi,Iwabuchi, Yoshiharu
, p. 504 - 506 (2007/10/03)
Herein, we describe the first asymmetric total synthesis of (-)-martinelline ((-)-2) and the second total synthesis of (-)-martinellic acid ((-)-1) by employing a tandem Mukaiyama-Mannich reaction/aminal cyclization as the key step. The Royal Society of C
Stereoselective syntheses of pharmaceutically relevant chiral tetrahydrofurans from (S)- and (R)-glyceraldehyde derivatives
Sharma,Punna, Sreenivas,Rajendra Prasad,Krishna, Palakodety Radna,Chorghade, Mukund S.,Ley, Steven V.
, p. 1113 - 1123 (2007/10/03)
A practically simple and flexible method of making chiral tetrahydrofurans of therapeutic relevance is reported from glyceraldehyde derivatives as chiral synthons. One of the stereocentres is derived from glyceraldehyde derivatives, while the other one is introduced by Sharpless asymmetric epoxidation using either (+)- or (-)-DIPT.
Stereoselective synthesis of chiral tetrahydrofurans with potent 5-LO inhibitory activity
Sharma,Punna, Sreenivas,Krishna, Palakodety Radha,Chorghade, Mukund S.,Ley, Steven V.
, p. 1125 - 1133 (2007/10/03)
Chiral glyceraldehydes have been exploited for the design of convenient and scalable synthetic approaches to chiral tetrahydrofurans, which have potential as potent 5-lipoxygenase (5-LO) inhibitors. The synthesis of all four possible stereoisomers by a general methodology is reported; wherein the chirons derived from the glyceraldehyde derivatives on reaction with homopropargyl ether, cyclization and further reactions gave the targets.
Stereoselective synthesis of (+)-SCH 351448: A unique ligand system for sodium, calcium, and other cations
Kang, Eun Joo,Cho, Eun Jin,Ji, Mi Kyung,Lee, Young Eun,Shin, Dong Mok,Choi, Soo Young,Chung, Young Keun,Kim, Jong-Seo,Kim, Hie-Joon,Lee, Sueg-Geun,Lah, Myoung Soo,Lee, Eun
, p. 6321 - 6329 (2007/10/03)
(+)-SCH 351448 (Na+ salt A) was synthesized employing ring-closing olefin metathesis reaction of an open diene diester intermediate for construction of the 28-membered macrodiolide structure. The open diene diester was prepared from the monomeric hydroxy carboxylic acid and two different olefin fragments. The monomeric hydroxy acid was synthesized via Julia-Julia coupling reaction of intermediates derived from the same olefinic fragments. Oxane units in these fragments were prepared by radical cyclization reactions of β-alkoxyacrylates. Analogous SCH 351448 salts incorporating other mono- and divalent cations may be prepared. Under acidic conditions, SCH 351448 (Na+ salt A) was the most stable complex, but SCH 351448 (Ca2+ salt) and (Na+ salt B) appear to be physiologically important species.
Reductive spiroannulation of nitriles with secondary electrophiles
Morin, Matthew D.,Rychnovsky, Scott D.
, p. 2051 - 2053 (2007/10/03)
(Chemical Equation Presented) The scope of reductive decyanation and spiroannulation reactions has been expanded to include secondary electrophiles for potentially useful transformations. Secondary phosphates and chlorides, as well as terminal epoxides, c
