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Biomimetic synthesis of Santalin A/B and Santarubin A/B

Ludwig-Maximilians-Universität München
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  • Fakultät Für Chemie Und Pharmazie
  • Chemistry


Biomimetic synthesis of Santalin A/B and Santarubin A/B Dissertation zur Erlangung des Doktorgrades der Fakultät für Chemie und Pharmazie der Ludwig-Maximilians-Universität München Biomimetic Synthesis of Santalin A/B and Santarubin A/B Synthetic Studies towards Santalin Y and Ayamenin E von Sebastian Strych aus München 2013 Erklärung: Diese Dissertation wurde im Sinne von §7 der Promotionsordnung vom 28. November 2011 von Herrn Prof. Dr. Dirk Trauner betreut. Eidesstattliche Versicherung: Diese Dissertation wurde eigenständig und ohne unerlaubte Hilfe erarbeitet. München, den 14. Juni 2013 ............................................................. Sebastian Strych Dissertation eingereicht am: 14. Juni 2013 Erstgutachter: Prof. Dr. Dirk Trauner Zweitgutachter: Prof. Dr. Paul Knochel Mündlich Prüfung am: 15. Juli 2013 i Abstract Red sandalwood has been admired for centuries for its beautiful color, hardness and durability, especially in Asian countries. The chemical nature of its colorants, however, has long been a mystery. Almost 160 years after Pelletier’s pioneering studies, the structures of the major pigments santalin A/B and santarubin A/B were elucidated by Arnone et al in 1975.[1] The following work is dealing with the synthesis of flavonoids and, in particular, with the members of the santalin family. The assembly of these complex natural products has been achieved in a longest linear sequence of 7 steps starting from commercially available starting material (Scheme 1). Scheme 1 – Efficient synthesis of santalin A from commercially available starting material. In general, the research project focuses on the development of a biomimetic synthesis of santalin A & B and santarubin A & B as well as on the complex, racemic oxafenestrane santalin Y.[2] Especially

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