Publikation: Enantioselective Total Synthesis of (+)-Pepluanol A
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Herein, we report an enantioselective and convergent total synthesis of (+)-pepluanol A, a structurally intriguing Euphorbia diterpenoid natural product featuring a 5/6/7/3-fused tetracyclic skeleton, from known building blocks in 11 steps. The successful strategy relies on a phenyl selenide-mediated Morita-Baylis-Hillman type reaction as a connective step, forging the precursor for the key intramolecular Diels-Alder reaction to construct the congested 5/6/7-tricyclic framework. A diastereoconvergent cascade starting with an acid-induced removal of the C1-MOM protecting group followed by a retro-aldol/aldol reaction resulted in the formation of a single diastereomer. This stereoconvergency allowed for the successful substrate-controlled diastereoselective cyclopropanation of an advanced intermediate to establish the full carboskeleton of (+)-pepluanol A (1).
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YUAN, Po, Tanja GAICH, 2022. Enantioselective Total Synthesis of (+)-Pepluanol A. In: Organic letters. American Chemical Society (ACS). 2022, 24, pp. 4717-4721. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.2c00961BibTex
@article{Yuan2022Enant-58032, year={2022}, doi={10.1021/acs.orglett.2c00961}, title={Enantioselective Total Synthesis of (+)-Pepluanol A}, volume={24}, issn={1523-7060}, journal={Organic letters}, pages={4717--4721}, author={Yuan, Po and Gaich, Tanja} }
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