118620-86-3Relevant academic research and scientific papers
Convergent Synthesis of the Dihydropyran Core Containing the C1-C15 Subunit of Sorangicin A Employing Gold(I)-Catalyzed Cyclization of an Allenic Alcohol
Raghavan, Sadagopan,Nyalata, Satyanarayana
supporting information, p. 10698 - 10706 (2016/11/29)
A convergent route to the C1-C15 subunit of sorangicin A is disclosed. The key steps include carbon-carbon bond formation using an α-chloro sulfide, regioselective hydrozirconation of an internal alkyne for the preparation of a trisubstituted iodoalkene, allene formation using the Myers-Movassaghi protocol, stereoselective reduction of allylic and propargylic ketones using Noyori's catalyst, and gold(I)-catalyzed cyclization of a β-hydroxy allene to construct the dihydropyran ring.
A stereoselective total synthesis of 7,8-O-isopropylidene iriomoteolide-3a
Zhang, Yao,Deng, Lisheng,Zhao, Gang
scheme or table, p. 4518 - 4526 (2011/07/29)
A stereoselective total synthesis of 7,8-O-isopropylidene iriomoteolide-3a has been achieved by using Yamaguchi esterification, Julia-Kocienski olefination, organocatalytic α-oxidation, and ring-closing metathesis reaction as key bond-forming steps.
Enantioselective total synthesis of peloruside a: A potent microtubule stabilizer
Ghosh, Arun K.,Xu, Xiaoming,Kim, Jae-Hun,Xu, Chun-Xiao
supporting information; experimental part, p. 1001 - 1004 (2009/04/07)
An enantioselective total synthesis of (+)-peloruside A (1) is described. Peloruside A (1) is a potent microtubule stabilizer with significant clinical potential. The synthesis is convergent and involves the assembly of C1-C10 segment 2 and C11-C24 segment 3 by a novel aldol protocol followed by Yamaguchi macrolactonization of the resulting seco-acid, selective methylation of hemi-ketal and removal of the protecting groups to peloruside A.
Total synthesis of (+)-Oocydin A: Application of the suzuki-miyaura cross-coupling of 1,1-Dichloro-1-alkenes with 9-alkyl 9-BBN
Roulland, Emmanuel
, p. 3762 - 3765 (2008/12/23)
(Chemical Equation Presented) Two sensitive fragments were coupled in the mild title reaction to create the Zchlorovinyl functionality of the target macrolide oocydin A (1; see scheme). Another highlight in the total synthesis of 1 was an efficient stereoselective Pd0-catalyzed cyclization to form the highly substituted tetrahydrofuran ring. Bz = benzoyl, TBS = tert-butyldimethylsilyl, MPM = 4-methoxyphenylmethyl.
Synthesis and biological activities of reveromycin A and spirofungin A derivatives
Shimizu, Takeshi,Usui, Takeo,Fujikura, Makoto,Kawatani, Makoto,Satoh, Tomoharu,Machida, Kiyotaka,Kanoh, Naoki,Woo, Je-Tae,Osada, Hiroyuki,Sodeoka, Mikiko
scheme or table, p. 3756 - 3760 (2009/04/04)
Various derivatives of reveromycin A, an inhibitor of eukaryotic cell growth, and spirofungin A, focusing on the 5S hydroxyl group and C18 hemisuccinyl group, were synthesized and their inhibitory effects on both the isoleucyl-tRNA synthetase activity and
The first total synthesis of naturally occurring (+)-gymnasterkoreayne F and its enantiomer
Carpita, Adriano,Braconi, Silvia,Rossi, Renzo
, p. 2501 - 2508 (2007/10/03)
The first total synthesis of naturally occurring (+)-gymnasterkoreayne F and its enantiomer is reported. The seven-step route to these two polyacetylenes in enantiomerically pure form involves the use of (+)-2,3-O-isopropylidene-l- threitol and (-)-2,3-O-isopropylidene-d-threitol, respectively, as the starting material and a Cadiot-Chodkiewicz reaction as a key step. The absolute configuration of (+)-gymnasterkoreayne F has been confirmed to be (2E,8S,Z). The natural product and its enantiomer have been found to exhibit modest cytotoxicity against the 60 human tumor cell lines of the National Cancer Institute.
Total synthesis of (-)-Neplanocin A by using lithium thiolate-initiated Michael-aldol tandem cyclization reaction
Ono, Masashi,Nishimura, Katsumi,Tsubouchi, Hiroshi,Nagaoka, Yasuo,Tomioka, Kiyoshi
, p. 8199 - 8203 (2007/10/03)
(-)-Neplanocin A (1), S-adenosylhomocystein hydrolase inhibitor, was synthesized. The characteristic of this synthesis is a stereoselective construction of five-membered ring of neplanocin A by intramolecular aldol reaction of the lithium enolate that was generated by conjugate addition of lithium thiolate. TBS-protected chiral ω-oxo-α,β-unsaturated ester 16, which was prepared from D-mannitol, was treated with 1.2 equiv of lithium be nzylthiolate in THF at -20 °C to give three separable cyclization products in good yields and stereoselectivity. After conversions of protective groups, the benzylsulfanyl part of 21 was removed by oxidation to sulfoxide and subsequent thermal elimination to give the requisite double bond. Through the functional group transformations of 30, total synthesis of (-)-neplanocin A (1) was accomplished.
The total synthesis of AB3217-A, a novel anti-mite substance, via intermolecular etherification and intramolecular glycosylation
Nakata,Tamai,Kamio,Kinoshita,Tatsuta
, p. 3057 - 3066 (2007/10/02)
The first total synthesis of AB3217-A has been achieved. The deacetylanisomycin unit, (3S,4S,5R)-3-benzyloxy-1-(benzyloxycarbonyl)-5-[(1R)-1-hydroxy-1-(4-me thoxyphenyl)methyl]-4-(2-tetrahydropyranyloxy)pyrrolidine (18), was prepared from dimethyl L-tartr
AN EFFECTIVE, PRACTICAL METHOD FOR THE SYNTHESIS OF CHIRAL PROPARGYL ALCOHOLS
Yadav, J. S.,Deshpande, Prasad K.,Sharma, G. V. M.
, p. 7033 - 7046 (2007/10/02)
The preparation of chiral propargyl alcohols (2) is described by LiNH2 or LDA induced double elimination of chiral epoxychlorides (4), derived from their corresponding epoxyalcohols (3) which are available easily by Sharpless asymmetric epoxidation of the primary allyl alcohols.Whereas, use of stoichiometric amount of base on 4 provides chirally enriched trans-1-chlorovinyl alcohols (14).
AN EXPEDITIOUS APPROACH FOR THE SYNTHESIS OF OPTICALLY ACTIVE ACETYLENIC ALCOHOLS
Yadav, J. S.,Chander, Madhavi C,Joshi, Bhalchandra V
, p. 2737 - 2740 (2007/10/02)
A practical method for the synthesis of acetylenic alcohols by base induced elimination of β-alkoxy chlorides is described.
