Journal
TETRAHEDRON LETTERS
Volume 121, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2023.154493
Keywords
Total synthesis; Tetracyclic spiroketal; Chiral pool approach; D -Glyceraldehyde
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A simple method was developed for constructing the tetracyclic spiroketal skeleton of Lycibarbarine A and B. By coupling the fragments through epoxide opening with tetrahydroquinoline under solvent-free conditions, followed by oxidation and TBAF-mediated silyl deprotection spiroketalization, the complete tetracyclic core present in these natural products was established.
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.
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