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First asymmetric total synthesis of (+)-sparteine.

Organic letters (2002-07-19)
Brenton T Smith, John A Wendt, Jeffrey Aubé
ABSTRACT

[reaction: see text] The total synthesis of (+)-sparteine was accomplished from 2,5-norbornadione in 15 steps and 15.7% overall yield. The key steps were two ring-expansion reactions, one involving an intramolecular Schmidt reaction and one using a novel variant of the photo-Beckmann rearrangement.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Bicyclo[2.2.1]hepta-2,5-diene, 98%