WebThe total synthesis of haliclonin A was accomplished. Starting from 3,5‐dimethoxybenzoic acid, a functionalized cyclohexanone fused to a 17‐membered ring was prepared through a Birch reduction/alkylation sequence, ring‐closing metathesis, intramolecular cyclopropanation, and stereoselective 1,4‐addition of an organocopper reagent to an … WebHaliclonin A (1), a macrocyclic diamide of a novel skeletal class, was isolated from the marine sponge Haliclona sp. collected from Korean waters. The structure of this …

Thieme E-Journals - Synlett / Abstract

WebA synthesis of a tetracyclic natural product, haliclonin A, was achieved. The cyclohexane ring was derived from 3,5‐dimethoxybenzoic acid, which was elaborated via Birch reduction, intramolecular cyclopropanation, and a reaction with an organocopper reagent. The lactam ring was constructed via reductive C−N bond formation. WebDec 1, 1998 · Enantioselective total synthesis of taxol has been accomplished. Coupling reaction of the optically pure A-ring hydroxy aldehyde with the aromatic C-ring fragment followed by Lewis acid mediated eight-membered B-ring cyclization gave the desired ABC endo-tricarbocycle. The C-ring moiety of this product was reduced under Birch conditions … ewing gallery knoxville

Organocatalytic, Asymmetric Total Synthesis of (-)-Haliclonin A.

WebThe core structure of haliclonin A, a 3-azabicyclo [3.3.1]nonane with a bridge that forms a 17-membered ring, was constructed. The synthesis features a ring-closing metathesis … WebMar 28, 2024 · Impressively, the total synthesis of macrocyclic alkaloid (−)-haliclonin A (63) in 2016 by Huang and collaborators highlights an unprecedented SmI 2-promoted intermolecular aldehyde–enone ... ewing gallery of art