@article { ISI:000265052800004, title = {Total synthesis of verbalactone: an efficient, carbohydrate-based approach}, journal = {Tetrahedron Letters}, volume = {50}, number = {18}, year = {2009}, month = {MAY}, pages = {2048-2049}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A carbohydrate-based strategy for the total synthesis of verbalactone has been described. (3R,5R)-3,5-dihydroxydecanoic acid was dimerised under Yamaguchi conditions to provide verbalactone in an overall yield of 17\% starting from 3-deoxy-1,2:5,6-di-O-isopropylidine-alpha-D-glucofuranose. (c) 2009 Elsevier Ltd. All rights reserved.

}, keywords = {Chiral pool approach, D-Glucose, verbalactone, Yamaguchi{\textquoteright}s macrolactonization}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2009.02.062}, author = {Salunke, Ganesh B. and Shivakumar, I. and Gurjar, Mukund K.} } @article {48730, title = {Concise approach for the synthesis of the tetracyclic framework of Lycibarbarines A and B}, journal = {Tetrahedron Letters}, volume = {121}, year = {2023}, month = {MAY }, type = {Article}, abstract = {

A simple approach for the construction of the tetracyclic spiroketal skeleton of Lycibarbarine A and B has been described. Employing a solvent free condition for epoxide opening with tetrahydroquinoline as a key reaction to couple both the fragments, an oxidation followed by TBAF-mediated silyl deprotection spiroketalization establishes the complete tetracyclic core present in these natural products. (c) 2023 Elsevier Ltd. All rights reserved.

}, keywords = {Chiral pool approach, D -Glyceraldehyde, Tetracyclic spiroketal, Total synthesis}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2023.154493}, author = {Shet, Manoj N. and Nechooli, Hemanth K. and Ramana, Chepuri V.} } @article {49507, title = {Studies on the stereoselective synthesis of sacubitril via a chiral amine transfer approach}, journal = {Chemistry-An Asian Journal}, volume = {20}, year = {2025}, month = {MAR }, type = {Article}, abstract = {

We present a comprehensive account of our efforts directed towards the synthesis of sacubitril, a neprilysin inhibitor used in combination with valsartan and marketed as Entresto (TM). Our initial approach to the formal synthesis of sacubitril employed a chiral pool strategy, utilizing (S)-pyroglutamic acid as a key building block and Cu(I)-mediated Csp2-Csp3 cross-coupling as a key transformation. Further investigations led to the development of chiral amine transfer (CAT) reagents-based stereoselective synthesis. This involved the E-selective construction of gamma-ylidene-butenolide from readily available biphenyl bromide and 4-pentynoic acid, the conversion of this butenolide to its ene-lactam using chiral amine, and substrate-controlled diastereoselective reduction of ene-lactam using Et3SiH or Pd/C, H2 (overall chiral amine transfer) as key transformations. Antipodal lactam intermediates were synthesized using corresponding chiral amines, and the stereochemical outcomes during the ene-lactam reduction with Et3SiH were rationalized by DFT studies.

}, keywords = {Chiral Amine Transfer (CAT) approach, Chiral pool approach, Sacubitril, stereoselective synthesis}, issn = {1861-4728}, doi = {10.1002/asia.202401223}, author = {Sadanande, Megha V. and Thorat, Sagar S. and Sharma, Himanshu and Singh, Geetika and Vanka, Kumar and Gonnade, Rajesh G. and Kontham, Ravindar} }