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Synthesis of an isomer of the renieramycin skeleton from L-tyrosine

✍ Scribed by Wei Liu; Wen Fang Dong; Xiang Wei Liao; Bao He Guan; Zhan Zhu Liu

Publisher
Journal of Heterocyclic Chemistry
Year
2011
Tongue
English
Weight
106 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A new approach that tried to obviate the use of bromine protection groups was studied to synthesize (−)‐renieramycin G from L‐tyrosine. It was found that the first intermolecular Pictet–Spengler reaction proceeded successfully to give the correct tetrahydroisoquinoline precursor 6. However, the second intramolecular Pictet–Spengler cyclization step failed to give the desired product, and an isomer of the skeleton of the renieramycins was obtained via 12 steps starting from L‐tyrosine. J. Heterocyclic Chem., (2011).

📜 SIMILAR VOLUMES

Total synthesis of (–)-MY 336a from L-ty
Total synthesis of (–)-MY 336a from L-tyrosine
✍ Xiang Wei Liao; Wen Fang Dong; Wei Liu; Bao He Guan; Zhan Zhu Liu 📂 Article 📅 2009 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 73 KB

## Abstract magnified image Using L‐tyrosine as a chiral starting material, we developed an efficient synthetic route to (–)‐MY 336a. A key step in the sequence is a highly regio‐ and diastereoselective intermolecular Pictet‐Spengler cyclization reaction between amino alcohol and benzyloxyacetalde