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

作者：Hong Allen Y; Vanderwal Christopher D

来源：Tetrahedron, 2017, 73(29): 4160-4171.

DOI：10.1016/j.tet.2016.11.004

• Cycloaddition
• Oxidation
• Alkaloids
• Total synthesis
• Natural products

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.

• 出版日期2017-7-20