111322-01-1Relevant articles and documents
Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II: Synthesis of C17-C29 Subunit and Completion of the Synthesis
Ochiai, Koji,Kuppusamy, Sankar,Yasui, Yusuke,Harada, Kenji,Gupta, Nishant R.,Takahashi, Yohei,Kubota, Takaaki,Kobayashi, Jun'ichi,Hayashi, Yujiro
, p. 3287 - 3291 (2016)
The total synthesis of 7,10-epimer of the proposed structure of amphidinolide N was accomplished. The requisite chiral C17-C29 subunit was assembled stereoselectively via Keck allylation, Shi epoxidation, diastereoselective 1,3-reduction, and a later oxidative synthesis of the THF framework. The C1-C13 and C17-C29 subunits were successfully coupled using a Enders RAMP "linchpin" as the C14-C16 three carbon unit, thereby controlling the chirality at C14 and C16. The labile allyl epoxy moiety was successfully constructed by Grieco-Nishizawa olefination at a final stage of the synthesis.
Effect of water on Keck's catalytic asymmetric allylations of aldehydes
Kurosu, Michio,Lorca, Miguel
, p. 1109 - 1112 (2005)
The complex generated from BINOL, Ti(i-PrO)4, and unactivated or a large amount of activated 4 ? MS in toluene is very effective in catalytic allylations of aldehydes using allyltributyltin. Allylations with 2.5 mol% of the catalyst provide hom
Synthesis of the Acyclic Carbon Skeleton of Filipin III
Brun, Elodie,Bellosta, Véronique,Cossy, Janine
, p. 8206 - 8221 (2016)
The synthesis of the carbon skeleton of filipin III, a polyenic macrolactone possessing 11 stereogenic centers, was achieved using a convergent strategy with the longest linear sequence of 19 steps starting from hexanal. Construction of the polyene was re
Asymmetric Synthesis of Atorvastatin Calcium through Intramolecular Oxidative Oxygen-Nucleophilic Bromocyclization
Wu, Yan,Liu, Min-Jie,Huang, Hai-Qing,Huang, Guan-Xin,Xiong, Fang-Jun,Chen, Fen-Er
, p. 3681 - 3688 (2017/07/22)
The stereocontrolled synthesis of atorvastatin calcium starting from commercially available d-aspartic acid using an intramolecular oxidative oxygen-nucleophilic bromocyclization of a homoallylic tert-butyl carbonate is described. This strategy allows the formation of the chiral syn-1,3-diol moiety with the desired stereochemistry, and provides a functionalized bromomethyl group for the construction of the atorvastatin side-chain with high regio- and diastereoselectivity. This route is attractive as it represents an efficient and environmentally sensitive approach to the large-scale synthesis of statins and their analogues.
Substitution dependent stereoselective construction of bicyclic lactones and its application to the total synthesis of pyranopyran, tetraketide and polyrhacitide A
Subba Reddy,Biradar, Dhanraj O.,Vikram Reddy,Yadav,Singarapu, Kiran Kumar,Sridhar
supporting information, p. 8832 - 8837 (2016/10/03)
A novel bicyclization strategy has been developed for the stereoselective synthesis of bicyclic lactones, i.e. 7-aryl or alkyl-2,6-dioxabicyclo[3.3.1]nonan-3-ones through a domino cyclization of (R)-3-hydroxyhex-5-enoic acid with an aldehyde in the presen
