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✦ LIBER ✦
The synthesis of a key intermediate en route to gelsemine: a program based on intramolecular displacement of the carbonoxygen bond of a strategic oxetane
✍ Scribed by Fay W Ng; Hong Lin; Qiang Tan; Samuel J Danishefsky
- Book ID
- 104232253
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 126 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The synthesis of key intermediate 30 en route to gelsemine has been accomplished from known aldehyde 10 via oxetane 19 featuring stereospecific Claisen rearrangement and Lewis acid-catalyzed oxetane ring opening.
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A new route to the enantiomerically pure azetidin-2-one 3, a key intermediate for the synthesis of trinems, has been developed, incorporating enantioselective intramolecular C-H insertion of ct-methoxycarbonyl-ot-diazoacetamide catalyzed by chiral Rh(II) complexes and diastereoselective arene hydrog