Our Recent Progress on the Intramolecular Diels–Alder Reaction Approach in Natural Products Synthesis: Synthetic Studies of the Octahydronaphthalene Substructure of Versipelostatins and the A/B/C‐Tricyclic Substructure of GKK1032s

Abstract

During this decade, the enantio- and stereoselective synthesis of natural products has been actively explored in the author's laboratory. In this account, the author outlines practical syntheses of the polycyclic substructures of two novel structurally formidable antibiotics, namely, the trans-fused octahydronaphthalene moiety of versipelostatins and the A/B/C-tricyclic decahydrofluorene moiety of GKK1032s. Both syntheses have been achieved with remarkable regio- and stereoselectivity via intramolecular Diels-Alder reactions using well-designed enantiomeric substrates.

Alkaloids from Marine Fungi: Promising Antimicrobials

“…Through labeling studies, Oikawa elucidated that GKK1032s are produced from l-tyrosine and nine acetate units, as well as l-methionine as a methyl donor [60]; however, more details on the biosynthesis route of these compounds are not known. On the other hand, many chemical syntheses were reported for GKK1032s or their intermediates [61][62][63], as well as for hirsutellones [64][65][66][67][68][69], which are also composed of this unique macroether ether ring. Pyrrospirones and pyrrocidines [70,71] were often neglected since the discovery of these four types of decahydrofluorene-type natural products over 20 years ago.…”