Stereoselective total synthesis of rubrenolide and rubrynolide |
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| Institution: | 1. Organic & Biomolecular Chemistry Division, CSIR—Indian Institute of Chemical Technology, Hyderabad 500 607, India;2. Division of Natural Products Chemistry, CSIR—Indian Institute of Chemical Technology, Hyderabad 500 607, India;1. Organic and Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore, Tamil Nadu 632 014, India;2. Division of High-Technology Materials Research, Korea Basic Science Institute, Busan Center, Busan 618 230, Republic of Korea;1. Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, Andhra Pradesh, India;2. Université de Rennes 1, Institut des Sciences Chimiques de Rennes, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes Cedex, France;1. Organic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India;2. Academy of Scientific and Innovative Research (AcSIR), Mathura Road, New Delhi 110 025, India;3. School of Science, Indrashil University, Kadi, Gujarat 382740, India |
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| Abstract: | The stereoselective total synthesis of rubrenolide and rubrynolide has been accomplished successfully. The synthetic strategy involves Evans alkylation and asymmetric CBS reduction to establish the required stereogenic centers. Other key steps involve Horner–Wadsworth–Emmons (HWE) olefination to construct the side chain, alkynylation to introduce terminal unsaturation in the side chain, and TEMPO-BAIB-mediated lactonization. |
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