Biomimetic Total Syntheses
of Borreverine and Flinderole
Alkaloids
- Publication date
- Publisher
Abstract
Dimeric
indole alkaloids represent a structurally unique class
of natural products having interesting biological activities. Recently,
we reported the first total synthesis of flinderoles B and C, structurally
unique and potent antimalarial natural products. Central to the design
of the approach and by virtue of a one-pot, acid-catalyzed dimerization
reaction, the route also provided total synthesis of the borreverine
class of natural products. This full account details the progress
of efforts that culminated in the protecting-group-free, six-step
total synthesis of all of the flindersia alkaloids: dimethylisoborreverine,
isoborreverine, flinderoles A–C, and their analogues. A biomimetic
approach featuring a scalable and catalytic formal [3 + 2] cycloaddition
and Diels–Alder reaction is outlined in detail. On the basis
of the experimental observations, a detailed mechanism has been proposed
for the dimerization of tertiary alcohol <b>28</b>
