876144-69-3Relevant academic research and scientific papers
Titanium(IV)-promoted regioselective nucleophilic ring-opening reaction of chiral epoxyallyl alcohols with acids as a tool for ready access to chiral 1,2,3-triol monoesters: Application to stereoselective total synthesis of macrolides
Radha Krishna, Palakodety,Ramana, D. Venkata
scheme or table, p. 674 - 679 (2012/03/22)
Titanium(IV)-promoted regioselective ring-opening reaction of chiral epoxy-allyl alcohols (Sharpless conditions as the key strategic step) is developed as a tool for ready access to chiral 5,6-dihydroxyoct-7-en-4-yl alkoxylates. Later, the synthetic utility of products thereof was demonstrated through the RCM based stereoselective synthesis of various natural products.
Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis
Reed, Sean A.,White, M. Christina
, p. 3316 - 3318 (2008/10/09)
A novel heterobimetallic Pd(II)sulfoxide/(salen)Cr(III)Cl-catalyzed intermolecular linear allylic C-H amination (LAA) is reported. This reaction directly converts densely functionalized α-olefin substrates (1 equiv) to linear (E)-allylic carbamates with good yields and outstanding regio- and stereoselectivities (>20:1). Chiral bis-homoallylic and homoallylic oxygen, nitrogen, and carbon substituted α-olefins undergo allylic C-H amination with good yields, excellent selectivities, and no erosion in enantiomeric purity. Streamlined routes to (E)-allylic carbamates that can be further elaborated to medicinally and biologically relevant allylic amines are also demonstrated. Valuable 15N-labeled allylic amines may be generated directly from allyl moieties at late stages of synthetic routes by using the readily available 15N-(methoxycarbonyl)-p-toluenesulfonamide nucleophile. Evidence is provided that this reaction proceeds via a heterobimetallic mechanism where Pd/sulfoxide mediates allylic C-H cleavage to form a π-allylPd intermediate, and (salen)Cr(III)Cl/BQ work together to promote functionalization with the nitrogen nucleophile. Copyright
Total synthesis and evaluation of the actin-binding properties of microcarpalide and a focused library of analogues
Fuerstner, Alois,Nagano, Takashi,Mueller, Christoph,Seidel, Guenter,Mueller, Oliver
, p. 1452 - 1462 (2008/02/04)
A comparative investigation shows that hydroxylated 10-membered lactones modeled around the fungal metabolites microcarpalide (1) and pinolidoxin (2) are endowed with selective actin-binding properties. Although less potent than the marine natural product
Synthesis of the C1-C21 southern hemisphere of the originally proposed structure of spirastrellolide A
Paterson, Ian,Anderson, Edward A.,Dalby, Stephen M.
, p. 3225 - 3228 (2007/10/03)
A stereocontrolled synthesis of the C1-C21 [6,6]-spiro-acetal-containing domain of the originally assigned structure of spirastrellolide A is reported, exploiting asymmetric boron aldol methodology and an alkyne addition to a C1
Lituarine synthetic studies. An efficient, stereocontrolled construction of the common c(7-19) tricyclic spiroketal fragment.
Smith 3rd.,Frohn
, p. 3979 - 3982 (2007/10/03)
A highly efficient, stereocontrolled synthesis of (+)-4, the common C(7-19) tricyclic spiroketal fragment of the lituarines A, B, and C (1-3), has been achieved. Highlights of the synthesis include a remarkably facile 6-endo cyclization to access the C(8-
