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Towards a total synthesis of (−)-cephalotaxine: construction of the BCDE-tetracyclic core

✍ Scribed by Stephen M Worden; Renameditswe Mapitse; Christopher J Hayes

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
82 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

The synthesis of the BCDE-tetracyclic core of (-)-cephalotaxine has been achieved in eight steps starting from N-Boc-L-proline methyl ester. An alkylidene carbene 1,5-CH insertion reaction was used as a key step in the stereocontrolled synthesis of the DE-spirocyclic fragment and an intramolecular Heck-type cyclisation was used to form the benzazepine ring, and hence complete the tetracycle formation.

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