Protecting-group-free total syntheses of (–)-integrifolin, (+)-8-epi-grosheimin and (+)-grosheimin
Abstract
The guaianolides represent an array of complex sesquiterpene natural products with the basic 5-7-5-ring structure. An efficient diastereoselective allylation of functionalized aldehyde with allyl bromolactone, translactonization and aldehyde-ene reactions paved an excellent path toward the protecting-group-free divergent total synthesis of (–)-integrifolin, (+)-8-epi-grosheimin and (+)-grosheimin. The common intermediate molecule ligustrin was synthesized and further extended through various compatible reactions to more complex guaianolides. The first asymmetric total synthesis of (–)-integrifolin was achieved. The presented study should expedite access to this fascinating bigger class of bioactive guaianolide natural products.
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