Total Synthesis of Lamellarins D, H, and R and Ningalin B

• Published in: Organic letters Vol. 13; no. 2; pp. 312 - 315
• Main Authors: Li, Qingjiang, Jiang, Jingqian, Fan, Aili, Cui, Yuxin, Jia, Yanxing
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 21.01.2011; Amer Chemical Soc
• Subjects: Aldehydes - chemistry; Alkaloids - chemical synthesis; Alkaloids - chemistry; Amines - chemistry; Catalysis; Chemistry; Chemistry, Organic; Coumarins - chemical synthesis; Coumarins - chemistry; Cyclization; Heterocyclic Compounds, 3-Ring - chemical synthesis; Heterocyclic Compounds, 3-Ring - chemistry; Heterocyclic Compounds, 4 or More Rings - chemical synthesis; Heterocyclic Compounds, 4 or More Rings - chemistry; Isoquinolines - chemical synthesis; Isoquinolines - chemistry; Marine Biology; Molecular Structure; Oxidation-Reduction; Physical Sciences; Pyrroles - chemical synthesis; Pyrroles - chemistry; Science & Technology; ALPHA 20-SULFATE; LUKIANOL-A; IMINIUM SALT DERIVATIVES; EFFICIENT SYNTHESIS; BIARYL COUPLING REACTION; PYRROLES; HYPERVALENT IODINE(III) REAGENT; G TRIMETHYL ETHER; MARINE NATURAL-PRODUCTS; ALKALOIDS
• DOI: 10.1021/ol1027877
• ISSN: 1523-7060; 1523-7052

A concise total synthesis of lamellarins D (7 steps), H (7 steps), and R (5 steps) and ningalin B (5 steps) is achieved starting from the corresponding aldehydes and amines. The synthesis features three oxidative reactions as key steps in a biomimetic manner, involving an AgOAc-mediated oxidative coupling reaction to construct the pyrrole core, a Pb(OAc)4-induced oxidative cyclization to form the lactone, and Kita’s oxidation reaction to form the pyrrole−arene C−C bond.