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Stereoselective Access to the Core Structure of Macroline-Type Indole Alkaloids: Total Synthesis of Macroline and
Vilas D Kadam1, Sridhara Shanmukha Rao B1, S K Mahesh
1Academy of Scientific & Innovative Research (AcSIR) , New Delhi , India.
Abstract:
Rapid synthesis of the pentacyclic core structure of macroline-type indole alkaloids, and its application in the total synthesis of macroline and alstomicine is described. The core structure was accomplished in a highly stereocontrolled manner via two key steps, Ireland-Claisen rearrangement and Pictet-Spengler cyclization, commencing from a readily available starting material l-tryptophan, which obviated the need of a particular chiral source as an external catalyst, reagent, or internal auxiliary.
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