First total synthesis of cichorine and zinnimidine

Abstract

The first total synthesis of the phytotoxins cichorine and zinnimidine is described. The synthetic tactics involve the sequential connection of the dense and diverse functionalities on the aromatic nucleus followed by a Parham cyclization process, giving rise to the lactam unit embedded in the title compound framework.

Identification and molecular genetic analysis of the cichorine gene cluster in Aspergillus nidulans

“…17,18 1 H NMR (DMSO- d 6 ): δ = 2.04 (3H, s), 3.83 (3H, s), 4.39 (2H, s), 6.81 (1H, s), 7.40 (1H, br s), 8.42 (1H, s), 9.76 (1H, s); 13 C NMR (DMSO- d 6 ): δ= 10.1, 43.9, 59.5, 103.7, 119.7, 123.8, 132.7, 154.2, 157.1, 170.6. For UV-Vis and ESIMS spectra, see Fig.…”

“…The compact, functionalized isoindolin-1-one framework was an attractive target for total synthesis. 17-18 Compounds featuring this framework have been shown to possess antimicrobial, 19 anti-HIV, 20 and antitumor properties. 21 …”

“…The compact, functionalized isoindolin-1-one framework was an attractive target for total synthesis. 17,18 Compounds featuring this framework have been shown to possess antimicrobial, 19 anti-HIV, 20 and antitumor properties. 21 Because the genome of A. nidulans has been sequenced and relatively well-annotated, 2 and because a straightforward gene targeting system has been developed for this species, 22,23 we could proceed to efficiently investigate the genes that are responsible for the formation of cichorine.…”

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

“…To cite some examples, cichorine [3] and zinnimidine [4] (Fig. 2) are simple isoindolinone alkaloids, for which total syntheses have been reported [5], and nuevamine (Fig. 2) is an isoindoloisoquinoline alkaloid [6–7].…”

A New Total Synthesis of Porritoxin

“…5 However, applications of this concept to the elaboration of five-membered lactams are scarce, 6 and as far as we are aware, utilization of carbamates as internal electrophiles has been confined thus far to acyclic systems. 6a, 7 We then reasoned that porritoxin 4 would be obtained by * To whom correspondence should be addressed. Fax: +33 (0)3 20 33 63 09.…”