Total synthesis of (−)-penicimutanin a and related congeners

Abstract

The first total synthesis of penicimutanin A (1) was achieved within 10 steps (LLS).

Marine natural products

“…280 Total synthesis of the proposed structure of chaunopyran A implied that revision of the absolute conguration to 786 is required, 281 whilst total synthesis of penicitide A both revised the previous partial stereochemical assignment and established the absolute conguration as 787. 282 Convergent and biomimetic syntheses of penicimutanin A, penicimutanolone and penicimutatin established the absolute congurations as 788-790 respectively 283 and syntheses of peribysins A-C and F-G revised the stereochemistry of peribysins A, C, F and G (to 791-794 respectively) and represented the rst syntheses of peribysins C, F and G. 284 Six step syntheses of the proposed and revised structures of (À)-versiquinazoline H led to correction of stereochemistry and the assignment of the absolute conguration as 795. 285 Synthesis of (À)-curvulamine C has been achieved from commercially available starting materials 286 and its yield from the producing fungus has been improved through addition of precursors alanine and proline to the culture.…”

Diketopiperazine Gels: New Horizons from the Self-Assembly of Cyclic Dipeptides

“…All these features make CDPs an attractive choice as biocompatible, green, functionalizable, and cheap building blocks for smart materials with a wide scope of applications from industry to medicine. The basic design is very simple: two amino acids bound together in a cyclic structure with a defined stereochemistry (i.e., LL, LD/DL, or DD) and the possibility to further derivatize the side chains [ 42 , 43 , 44 , 45 , 46 ] of selected amino acids [ 47 , 48 , 49 , 50 ], as widely applied in nature [ 51 , 52 , 53 , 54 , 55 , 56 ].…”

Structural and Data Science-Driven Analysis to Assess Substrate Specificity of Diketopiperazine Reverse Prenyltransferase NotF: Cascade Biocatalytic Synthesis of (–)-Eurotiumin A

“…The incredible structural diversity and potent biological activity of C2 reverse prenylated diketopiperazine (DKP) natural products (NPs) has inspired the development of selective chemical methods for reverse prenyltransfer as an entry point for synthesis of prenylated NPs and their analogues. [1][2][3][4][5][6][7][8] State-of-the-art synthetic methods for C2 reverse prenylation of tryptophan substituents is typically performed at an early stage, requires multiple protecting groups, and fresh preparation of a prenylating reagent, such as prenyl-9-BBN. 6 The development of a general, biocatalytic method for prenyltransfer, i.e., a site-selective prenyltransferase (PT) with broad substrate scope, would provide an efficient method for installation of prenyl functionalities that circumvents the necessity of protecting groups and enables late-stage diversification with additional tailoring enzymes.…”