Stereochemical Determination of Thuggacins A–C, Highly Active Antibiotics from the Myxobacterium Sorangium cellulosum

Abstract

Chemistry and biology meet in the structure elucidation of the antibiotics thuggacins A–C. The absolute configuration of all stereogenic centers in the thuggacins was confirmed through a combination of chemical derivatization, NMR analysis, molecular modeling, and bioinformatic analysis of the thuggacin biosynthetic genes.

A Common Synthetic Protocol for the Cyclic and Acyclic Core of Migrastatin, Isomigrastatin, and Dorrigocin via a Chiral β‐Hydroxy‐γ‐butyrolactone Intermediate

“…It is noteworthy that lactone 7 is characterized by three important features: i) an alk‐1‐en‐3,4‐diol6 system (numbering based on the olefin); ii) three contiguous chiral centres (a very common pattern that is found in tedanolides,7a amphidinolides,7b bafilomycins,7c,7d thuggacins,7e and benzoquinone ansamycin antibiotics,7f etc. ); and most importantly iii) terminal olefin and ester orthogonal functionalities, which could be used as handles to install further functionalities required for the synthesis of natural products.…”

A new seco-pimarane diterpene and four new β-resorcylic acid lactones from a fungicolous Hypomyces subiculosus

“…Its molecular formula was determined to be C 20 (Fig. 2) from H-1 to C-3 and C-5, from H 2 -2 to C-4 and C-10, from H-3 to C-1 and C-5, H-5 to C-1, C-3, C-4, C-6, C-7, C-9, and C-10, from H-7 to C-5, C-6, C-8, and C-9, from H 3 -18 (19) to C-3, C-4, and C-5, and from H 3 -20 to C-1, C-5, C-9 and C-10 established 5,7-dihydroxy-4a,8,8trimethyl-4a,5,6,7,8,8a-hexahydronaphthalene-1,4-dione skeleton ( Fig. 3).…”

Synthesis of Macrocyclic Lactams and Lactones Containing Sulfur and Nitrogen

“…[25,26] При стоянии в растворе туггацин А (41) претерпевает ацильный сдвиг, приводя к смеси туггацинов В (42) и С (43). [25] Ретросинтетический анализ молекул туггацинов 41-43 предполагал образование их из двух блок-синтонов 44 и 45.…”