Stereocontrolled reduction of an oxazepinohexahydroindolo[2,3-a]quinolizine derivative: asymmetric total synthesis of (+)-tacamonine
β Scribed by Bruno Danieli; Giordano Lesma; Daniele Passarella; Alessandro Sacchetti; Alessandra Silvani
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 129 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Efficient, stereocontrolled total synthesis of the title compound is described, starting from enantiopure intermediates. A key step was the diastereoselective catalytic hydrogenation of a pentacyclic oxazepinohexahydroindolo[2,3-a]quinolizine derivative.
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## Abstract For Abstract see ChemInform Abstract in Full Text.
The relative configurations of 1,8-stereogenic centres can be controlled by coupling the tin(IV) chloride promoted reactions of aldehydes with 4-alkoxypent-2-enylstannanes, which proceed with excellent 1,5-induction, with a 2,3-Wittig rearrangement: this approach has been used to complete a diastere