Application to the Enantioselective Synthesis of (-)-Isoretronecanol and (+)-Laburnine. -Compound (I) is an adduct of a stereoselective radical addition of a tertiary amine with (5R)-5-menthyloxy-2[5H]-furanone. It is readily transformed to (+)-laburnine (IV) in a three-step sequence. Similarly, (-
Stereoselective radical addition of tertiary amines to (5R)-5-menthyloxy-2[5H]-furanone: Application to the enantioselective synthesis of (−)-isoretronecanol and (+)-laburnine
✍ Scribed by Samuel Bertrand; Norbert Hoffmann; Jean-Pierre Pete
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 138 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The adducts of a stereoselective radical addition of tertiary amines with (5R)-5-menthyloxy-2[5H]-furanone were transformed very efficiently into enantiomerically pure pyrrolizidine and indolizidine alkaloids, through a three steps sequence.
📜 SIMILAR VOLUMES
Tertiary amines derived from pyrrolidines can be added veD' efficiently (isolated yields up to 94%) to (SR)-5-mentyloxy-2[5H]-furanone. The addition, which follows a radical chain mechanism initiated by a photoinitiated electron transfer (PET) from the tertiary amine to the excited aromatic ketone,
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