161024-43-7

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InChI:InChI=1/C8H15NO2/c10-7-5-9-4-2-1-3-6(9)8(7)11/h6-8,10-11H,1-5H2/t6-,7-,8-/m0/s1

Upstream product

• 4541-15-5 5-(benzyloxy)-1-pentanol 
• 78999-24-3 5-benzyloxy-1-pentanal 
• 1420298-18-5 (2S,3S,4S)-1-(tert-butyloxycarbonyl)-3,4-bis(benzyloxy)-2-ethenylpyrrolidine 
• 503551-13-1 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-methylgalactopyranose 
• 1607822-16-1 (2S,3S,4S)-2-(4-(benzyloxy)but-1-en-1-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)-1-((R)-1-phenylethyl)pyrrolidine 

Relevant academic research and scientific papers

Stereoselective addition of Grignard reagents to sulfinimines derived from tartrate diol (threitol): Generation of chiral building blocks for the collective total synthesis of lentiginosine, conhydrine and methyldihydropalustramate

A systematic investigation of the addition of Grignard reagents to sulfinimines derived from tartaric acid diol was undertaken. It was observed that the chirality of the inherent tartrate moiety influences the diastereoselectivity of the resultant sulfinamides formed in the reaction. The formed products serve as excellent building blocks for the synthesis of natural products. This has been demonstrated in the collective total synthesis of lentiginosine, (+)-α-conhydrine and methyldihydropalustramate.

Tsuji–Trost Reaction of Non-Derivatized Allylic Alcohols

Palladium-catalyzed allylic substitution of non-derivatized enantioenriched allylic alcohols with a variety of uncharged N-, S-, C- and O-centered nucleophiles using a bidentate BiPhePhos ligand is described. A remarkable effect of the counter ion (X) of the XPd[κ2-BiPhePhos][η3-C3H5] was observed. When ClPd[κ2-BiPhePhos][η3-C3H5] (complex I) was used as catalyst, non-reproducible results were obtained. Study of the complex by X-ray crystallography, 31P NMR spectroscopy, and ESI-MS showed that a decomposition occurred where one of the phosphite ligands was oxidized to the corresponding phosphate, generating ClPd[κ1-BiPhePhosphite-phosphate][η3-C3H5] species (complex II). When the chloride was exchanged to the weaker coordinating OTf? counter ion the more stable Pd[κ2-BiPhePhos][η3-C3H5]++[OTf] ? (complex III) was formed. Complex III performed better and gave higher enantiospecificities in the substitution reactions. Complex III was evaluated in Tsuji–Trost reactions of stereogenic non-derivatized allylic alcohols. The desired products were obtained in good to excellent yields (71–98 %) and enantiospecificities (73–99 %) for both inter- and intramolecular substitution reactions with only water generated as a by-product. The methodology was applied to key steps in total synthesis of (S)-cuspareine and (+)-lentiginosine. A reaction mechanism involving a palladium hydride as a key intermediate in the activation of the hydroxyl group is proposed in the overall transformation.

Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach

The synthesis of the indolizidine alkaloid, (+)-lentiginosine, is described. A key feature of the preparative route is the efficient and stereoselective construction of a dihydroxylated pyrrolidine via Sharpless asymmetric dihydroxylation of an aziridine-

Synthesis of (+)-Lentiginosine and Its Pyrrolizidine Analogue Based on Intramolecular Cyclization of α-Sulfinyl Carbanions

A synthesis of (+)-lentiginosine and its pyrrolizidine analogue was accomplished in six steps, starting from L-(+)-tartaric acid. The key step of these syntheses involves the intramolecular cyclization of α-sulfinyl carbanions for the construction of the indolizidine or pyrrolizidine ring.

Practical synthesis of trans-dihydroxybutyrolactols as chiral C4 building blocks and their application to the synthesis of polyhydroxylated alkaloids

Practical syntheses of trans-dihydroxybutyrolactols 2a, 2b and 2c from inexpensive chiral pool compounds l-ascorbic, d- and l-tartaric acid have been achieved on a multigram-scale. The synthetic applications of these chiral building blocks have been demonstrated in the efficient total or formal synthesis of polyhydroxylated alkaloids (+)-lentiginosine and (-)-deacetylanisomycin in concise routes. The Royal Society of Chemistry 2013.

A diastereoselective cyclic imine cycloaddition strategy to access polyhydroxylated indolizidine skeleton: Concise syntheses of (+)-/(-)-lentiginosines and (-)-2-epi-steviamine

We describe in this paper the development of a novel diastereoselective cyclic imine cycloaddition strategy to access the polyhydroxylated indolizidine skeleton and its application in the concise syntheses of (+)-/(-)-lentiginosines and (-)-2-epi-steviamine.

Enantiospecific total synthesis of (+)-lentiginosine

A facile synthesis of (+)-lentiginosine is accomplished from L-(+)-tartaric acid. Key transformations in the synthesis include the elaboration of a-oxo amide derived from tartaric acid.

A concise enantioselective synthesis of (+)-lentiginosine

A high yielding enantioselective synthesis of the indolizidine alkaloid, (+)-lentiginosine, has been described based on asymmetric aza-Cope rearrangement and the l-proline catalyzed α-aminooxylation of aldehydes. The strategy also makes use of ring-closin

Total synthesis of (+)-lentiginosine from d-glucose

A total synthesis of (+)-lentiginosine, a potent and selective amyloglucosidase inhibitor, is reported from a d-glucose-derived epoxide in 38% overall yield. In this synthesis, ambient conditions and readily available starting materials and reagents are used.

Sterically biased 3,3-sigmatropic rearrangement of chiral allylic azides: Application to the total syntheses of alkaloids

(Chemical Equation Presented) We describe a tandem Mitsunobu/3,3- sigmatropic rearrangement of allylic azides on a chiral auxiliary system that favors one regioisomer thanks to its exceptional steric bias. The sequence may be completed by the oxidative cleavage of the auxiliary or by a ring-closing metathesis reaction that produces a carbo-or heterocycle directly and a recyclable form of the chiral auxiliary. Applications of the methodology to the total synthesis of (+)-coniine, (+)-lentiginosin, and (+)-pumiliotoxin C are reported.