@article { ISI:000287635800023, title = {Stereoselective formal total synthesis of novel antibiotic (-)-centrolobine}, journal = {Heterocycles}, volume = {80}, number = {1}, year = {2010}, month = {JAN}, pages = {219-227}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

A concise and stereoselective formal total synthesis of (-)-centrolobine is achieved utilizing Mioskowski{\textquoteright}s Lewis acid mediated epoxide opening followed by ring-closing metathesis as the key reaction.

}, keywords = {antibiotic, Centrolobine, Keck allylation, Ring-closing metathesis, Sharpless asymmetric epoxidation}, issn = {0385-5414}, doi = {10.3987/COM-08-S(S)1}, author = {Mohapatra, Debendra K. and Pal, Rita and Rahaman, Hasibur and Gurjar, Mukund K.} } @article { ISI:000358099300015, title = {Enantioselective synthesis of (+)-hygroline and (+)-pseudohygroline via Keck allylation and CBS reduction}, journal = {Tetrahedron Letters}, volume = {56}, number = {32}, year = {2015}, month = {AUG}, pages = {4704-4705}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An enantioselective synthesis of (+)-hygroline and (+)-pseudohygroline has been achieved in high optical purity (98\% ee) from readily available 1,4-butanediol. The synthesis strategy employs a Keck allylation, CBS reduction, and Wacker oxidation. (C) 2015 Elsevier Ltd. All rights reserved.

}, keywords = {CBS reduction, Keck allylation, Pyrrolidines, Wacker oxidation}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2015.06.012}, author = {Bhoite, Shubhangi P. and Kamble, Rohit B. and Suryavanshi, Gurunath M.} } @article {48008, title = {Studies toward the total synthesis of (+)-neopeltolide using N-heterocyclic carbene-catalyzed oxo-acyloxylation/reductive oxa-Michael addition strategy}, journal = {Bulletin of the Korean Chemical Society}, volume = {43}, year = {2022}, month = {OCT}, pages = {1169-1172}, type = {Article}, abstract = {

This article describes a concise synthesis of two important fragments (tetrahydropyran [THP] and ketone moieties) of the cytotoxic macrolide (+)-neopeltolide in 10 long linear steps in enantiomerically pure form. Asymmetric Keck allylation to install the required C11 and C13 stereocenters, N-heterocyclic carbene (NHC)-catalyzed oxoacyloxylation to functionalize alkenes, and reductive oxa-Michael addition to construct 2,6-difunctionalized THP unit intramolecularly are the important steps in synthetic efforts. Finally, Keck asymmetric allylation and Lewis acid-catalyzed diastereoselective allylation of the aldehyde were sequentially employed to establish the stereocenters at C11 and C13 positions, respectively.

}, keywords = {(+)-neopeltolide, Keck allylation, Macrolide, NHC-catalyzed oxoacyloxylation, reductive oxa-Michael addition}, issn = {0253-2964}, doi = {10.1002/bkcs.12604}, author = {Reddi, Rambabu N. and Sudalai, Arumugam and Jo, Changbum} }