Asymmetric Total Syntheses of Macroline-Type Alkaloids Alstomicine and Alstofolinine A

Dedicated to Prof. Guo-Qiang Lin, on the occasion of his 80^th birthday.

Abstract

Macroline-type monoterpenoid indole alkaloids represent a fascinating class of natural products with polycyclic structures, diverse biological and pharmacological activities. Herein the asymmetric total syntheses of two of this type alkaloids, (–)-Alstomicine and (–)-Alstofolinine A are reported. Notably, these two alkaloids are divergently synthesized from a common indole-fused azabicyclo[3.3.1]nonane intermediate, which was easily obtained via a Mannich-type cyclization. An SmI₂-mediated Reformatsky reaction and a Pd-catalyzed carbonylative lactonization are employed to construct the lactone moieties presented in Alstomicine and Alstofolinine A, respectively.

Key words

macroline alkaloids - natural products - total synthesis - cyclizations - bridged rings

Publication History

Received: 14 April 2023

Accepted: 10 May 2023

Accepted Manuscript online:
10 May 2023

Article published online:
03 July 2023

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