Biselyngbyolides A & C: their total synthesis and anticancer activities

Abstract

Convergent strategies for the first total synthesis of biselyngbyolide C and an alternative route for the total synthesis of biselyngbyolide A have been developed. The key strategic feature of this...

Marine natural products

“…The first total syntheses of 19 cyanobacteria-derived compounds were reported during 2020, including ambigols A–E, 123 biseokeaniamides A–C, 124 5′- O -α- d -glucopyranosyl tubercidin, 125 kakeromamide A, 126 anaephenes A and B, 127 lyngbyoic acid, 128 anaenamides A 273 and B 274 , 110 and anaenoic acid 275 , 110 biselyngbyolide C, 129 tutuilamide A 262 , 130 and kasumigamide 307 . 131 The synthesis of several kasumigamide stereoisomers enabled the structure revision of this MNP.…”

Site-directed late-stage diversification of macrocyclic nannocystins facilitating anticancer SAR and mode of action studies

“…To our delight, the ring closure product turned out solely as an 8 E stereoisomer, thus adding to the robustness of Heck cross-coupling in macrocycle synthesis. 46–51 Final removal of the TBS group led smoothly to 8 in 90% yield. Advancing to the second stage (Scheme 1), 8 reacted separately with different acyl donors such as acid anhydrides (for 9a and 9d ), acyl chlorides (for 9b and 9c ), and carboxylic acids (for 9e–9n ), under three coupling conditions (see the table inset in Scheme 1; also refer to the experimental section for synthetic details).…”

Structure–Activity Relationship Study of Biselyngbyolide B Reveals Mitochondrial Fission-Induced Cytotoxicity in Cancer

“…The requisite purified esters were then subjected to Heck macrocyclization 35,36 to furnish pure compounds 48 and 49, respectively. The esterified products bearing inseparable Zvinyl iodide did not participate in Heck cyclization, similar to our earlier observation.…”

“…Suenaga and co-workers disclosed elegant synthetic routes for the total synthesis of biselyngbyolide A ( 3 ), biselyngbyolide B ( 1 ), and biselyngbyaside ( 2 ) using the Stille macrocyclization strategy. We have also developed synthetic routes for the total synthesis of biselyngbyolide B ( 1 ), biselyngbyolides A ( 3 ) and C ( 5 ) adopting the Heck macrocyclization approach, whereas Maier et al reported a successful total synthesis of biselyngbyolide B ( 1 ) following the same macrocyclization strategy.…”