@article { ISI:000321490900014, title = {Synthesis of a sex pheromone of the longtailed mealybug, pseudococcus longispinus}, journal = {Synthesis-Stuttgart}, volume = {45}, number = {12}, year = {2013}, month = {JUN}, pages = {1689-1692}, publisher = {GEORG THIEME VERLAG KG}, address = {RUDIGERSTR 14, D-70469 STUTTGART, GERMANY}, abstract = {

The synthesis of a recently identified and highly active sex pheromone of the longtailed mealybug, Pseudococcus longispinus is reported. A concise synthetic route, use of the under explored Meyer-Schuster rearrangement, Claisen rearrangement, and ring-closing metathesis are the highlights of this work.

}, keywords = {Acylation, Metathesis, pheromones, rearrangement, Total synthesis}, issn = {0039-7881}, doi = {10.1055/s-0033-1338450}, author = {Kurhade, Suresh E. and Siddaiah, V. and Bhuniya, Debnath and Reddy, D. Srinivasa} } @article {48075, title = {Revisiting classical pummerer cyclization reaction: a key strategy for the synthesis of (+/-)-quinagolide}, journal = {ChemistrySelect}, volume = {7}, year = {2022}, month = {JUL}, pages = {e202201600}, type = {Article}, abstract = {

A formal synthesis of (+/-)-quinagolide using beta-alanine as a starting material has been achieved. Late stage intramolecular classical Pummerer reaction has been used as a key synthetic tool to construct octahydrobenzo[g]quinoline skeleton of quinagolide. Conjugative reduction of olefin, regioselective C-alkylation over O-alkylation of beta-ketoester followed by retro-Dieckmann/ Dieckmann reaction sequence has been used as a key reaction sequence to achieve prerequisite sulfoxide for the Pummerer reaction. While revisiting the classical Pummerer reaction, the one-pot sequential thionium ion induced cyclocarbamation followed by N-carbamate deprotection and Friedel-Crafts type Pummerer cyclization was observed as an important finding of the present work.

}, keywords = {Alkylation, Cyclocarbamation, Hyperprolactinemia, rearrangement, Thionium ion}, issn = {2365-6549}, doi = {10.1002/slct.202201600}, author = {Chavan, Subhash P. and Kawale, Sanket A. and Tripathi, Anupam and Kadam, Appasaheb L. and Gonnade, Rajesh G.} } @article {48266, title = {FeCl2-catalyzed rearrangement of aryl peroxyoxindole into 1,3-benzooxazin-4-One}, journal = {Advanced Synthesis \& Catalysis}, volume = {365}, year = {2023}, month = {FEB}, pages = {515-521}, type = {Article}, abstract = {

We report an FeCl2-catalyzed radical rearrangement of aryl peroxyoxindoles into 1,3-benzooxazin-2-ones to obtain a variety of aryl substituted 1,3-benzooxazin-4-ones in moderate to good yields. Mechanistically, this skeletal rearrangement of peroxyoxindoles proceeded via radical pathway and was well supported with a series of experimental findings and DFT studies.

}, keywords = {1, 3-Benzooxazin-4-one, FeCl2, Peroxyoxindole, rearrangement, Ring expansion}, issn = {1615-4150}, doi = {10.1002/adsc.202201308}, author = {Mohanta, Nirmala and Samal, PragnyaParamita and Krishnamurty, Sailaja and Gnanaprakasam, Boopathy} }