83458-92-8Relevant articles and documents
Stereoselective synthesis of dendrodolide-L
Bujaranipalli, Sheshurao,Das, Saibal
, p. 254 - 260 (2017/03/01)
An efficient stereoselective total synthesis of 12-membered macrolide dendrodolide L has been achieved. The key reactions involved are Keck asymmetric allylation, Jacobsen's hydrolytic kinetic resolution, Sharpless asymmetric epoxidation, Mitsunobu reaction and ring-closing metathesis reaction.
A formal total synthesis of (-)-brevisamide, a marine monocyclic ether amide
Lee, Jungmee,Oh, Hong-Se,Kang, Han-Young
, p. 1099 - 1102 (2015/02/19)
A formal total synthesis of (-)-brevisamide, a monocyclic ether amide with architecturally unique structural features, has been achieved. The tetrahydropyran core part of the target was synthesized by the aldol reaction followed by ring-closing metathesis using the Grubbs second generation catalyst. After the stereochemistry at the carbon center bearing the hydroxy group was adjusted, the carbon-carbon double bond was stereoselectively reduced by catalytic hydrogenation. Finally, introduction of the amino group was followed by acetylation, which provided the desired advanced intermediate.
A practical total synthesis of (+)-spirolaxine methyl ether
Yadav,Sreenivas,Srinivas Reddy,Subba Reddy
supporting information; experimental part, p. 8307 - 8310 (2011/02/27)
An efficient and practical total synthesis of (+)-spirolaxine methyl ether is described. The phthalide-aldehyde 3 has been prepared via the Diels-Alder reaction between 1,4-unconjugated diene 5 and a long-chain acetylenic dienophile 6. The carbon framework of spiroketal sulfone 4 has been constructed from monobenzyl protected 1,5-pentanediol and the stereochemistry in both the phthalide portion and the spiroketal portion has been established by the Sharpless asymmetric epoxidation.
The stereoselective total synthesis of (+)-stagonolide B
Srihari, Pabbaraja,Kumaraswamy, Boyapelly,Somaiah, Ragam,Yadav, Jhillu S.
experimental part, p. 1039 - 1045 (2010/04/29)
The stereoselective total synthesis of the nonenolide, (+)-stagonolide B is described. The key steps involve epoxide homologation, hydrolytic kinetic resolution and ring-closing metathesis.
Stereoselective synthesis of a key intermediate of (-)-apicularen A
Yadav,Niranjan Kumar,Prasad
, p. 1175 - 1178 (2008/02/02)
Progress towards the stereoselective formal synthesis of (-)-apicularen A is described. The convergent approach involves the assembly of aliphatic and aromatic fragments via Grubbs's cross metathesis. Other key reactions in the strategy include Sharpless
Enantioselective total synthesis of aigialomycin D
Lu, Jiangping,Ma, Junying,Xie, Xingang,Chen, Bo,She, Xuegong,Pan, Xinfu
, p. 1066 - 1073 (2007/10/03)
An efficient, convergent approach for the total synthesis of aigialomycin D 1 is described. Key features of the synthetic strategy include (a) a Sharpless asymmetric epoxidation reaction and selective opening of a 2,3-epoxy alcohol to elaborate the two hy
Synthesis of diastereomerically and enantiomerically pure 2,3-disubstituted tetrahydrofurans using a sulfoxonium ylide
Schomaker, Jennifer M.,Pulgam, Veera Reddy,Borhan, Babak
, p. 13600 - 13601 (2007/10/03)
Nucleophilic substitution reactions of 2,3-epoxy alcohols, easily prepared via Sharpless asymmetric epoxidation chemistry, offer access to a wide variety of enantiomerically pure compounds. In this communication, we describe the use of a Payne rearrangement to control regioselectivity in the ring-opening of a series of 2,3-epoxy alcohols with dimethylsulfoxonium methylide to yield diastereomerically and/or enantiomerically pure disubstituted tetrahydrofuran rings. The factors influencing the success and substitution pattern of the THF ring products are discussed, including steric, electronic, and solvent effects. Copyright
Synthetic studies on the dienophile unit of methyl isosartortuoate. Part 1: Assembly of the acyclic precursor
Hong, Zhangyong,Chen, Xinchao,Xu, Xingxiang
, p. 485 - 488 (2007/10/03)
A strategically functionalized compound, as the acyclic precursor of the dienophile unit of methyl isosartortuoate has been synthesized, and its stereochemistry was also assigned.
γ-Butyrolactone, an Alternative Source of Chiral Iodo Derivatives.
Kermadec, Dominique,Prudhomme, Michelle
, p. 2757 - 2758 (2007/10/02)
An efficient synthesis of (3S) 1,3-di-tert-butyldimethylsilyloxy-6-iodohexane, a chiral iodo derivative useful for the preparation of functionalised 1,7-dioxaspiroundecanes from γ-butyrolactone is described.
Synthetic Studies towards Halichondramides, and Related Novel tris-Oxazole Containing Macrolides from Marine Organisms. A Concise Route to the Keto-triol Formyl Enamine Moiety.
Kiefel, Milton J.,Maddock, John,Pattenden, Gerald
, p. 3227 - 3230 (2007/10/02)
A synthesis of the keto-triol formyl enamine moiety (3) in the marine metabolite halichondramide (1) is described.The synthesis features judicious application of the Evans chiral aldol protocol in combination with the controlled ring opening of chiral α-e
