Divergent Total Syntheses of Enmein-Type Natural Products: (–)-Enmein, (–)-Isodocarpin and (–)-Sculponin R

04 April 2018, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Divergent total syntheses of enmein-type natural products, (–)-enmein, (–)-isodocarpin and (–)-sculponin R, have been achieved in a concise fashion. Key features of the strategy include (a) an efficient early-stage cage formation to control succeeding diastereoselectivity, (b) an one-pot acylation/akylation/lactonization to construct the C-ring and C8 quarternary center, (c) a reductive alkenylation approach to construct enmain D/E rings and (d) a flexible route to allow divergent syntheses of three natural products.

Keywords

terpenes
enmein
divergent synthesis
cage formation
total synthesis

Supplementary materials

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