A facile synthesis of bronchodilatory pyrrolo[2,1-b]quinazoline alkaloids by azidoreductive cyclizationstrategy employing TMSCl−NaI and bakers' yeast is described. Both the chemical and enzymaticmethods are mild and take place at room temperature in good yields. Further, synthesis andresolution of vasicinone has been carried out by employing different lipases. It has been observedthat lipase PS provides acetate of (S)-vasicinone in 98% ee.