PubAg

Main content area

A sequential cycloaddition strategy for the synthesis of Alsmaphorazine B traces a path through a family of Alstonia alkaloids

Author:
Hong, Allen Y., Vanderwal, Christopher D.
Source:
Tetrahedron 2017 v.73 pp. 4160-4171
ISSN:
0040-4020
Subject:
Alstonia, aldehydes, biosynthesis, chemical reactions, chemical structure, indole alkaloids
Abstract:
Driven by a new biogenetic hypothesis, the first total synthesis of alsmaphorazine B and several related indole alkaloids has been achieved. Numerous early approaches proved unsuccessful owing to unproductive side reactivity; nevertheless, they provided important clues that guided the evolution of our strategy. Critical to our success was a major improvement in our Zincke aldehyde cycloaddition strategy, which permitted the efficient gram-scale synthesis of akuammicine. The sequential chemoselective oxidations of akuammicine leading up to the key oxidative rearrangement also yielded several biogenetically related indole alkaloids en route to alsmaphorazine B.
Agid:
5705546