Abstract
The presence of a borane axial group in compound 14 induces a regio and stereospecific 1O 2 cycloaddition at low temperature. This selectivity together with that obtained during the lithium liquid ammonia reduction of the 4aβ-hydroxyenone 6, allows a short and stereospecific synthesis of the (±) epi-7,7a tecomanine 5, an unnatural and undescribed isomer of the tecomanine 1.
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