Interesting stereoselectivity of intramolecular Diels-Alder reactions leading to 5-carbomethoxy yohimbine systems

Total Synthesis of (±)‐Haliclonacyclamine C

“…[61][62][63] The tetracyclic ring system was completed by lactamization to afford azocine 2.64. [64][65][66] Leonard,83,84 Markό, 85,86 as well as the total syntheses and approaches outlined above, the manzamines have clearly been the target of choice among the synthetic community. However, sarain A (1.5) is another structurally intriguing pentacyclic natural product presumably biosynthesized from 3-alkylpyridines that has also caught the attention of synthetic investigators.…”

Total Synthesis of (±)‐Haliclonacyclamine C

“…Among all 3-alkylpiperidine the synthesis of manzamines has undoubtedly been studied more than any other group of alkaloids isolated from this family of natural products. With the total synthesis of manzamine C by Hino 65,71 and Gerlach, 72 the approaches to manzamine A by Yamamura, [73][74][75][76][77][78] Clark, 79,80 Simpkins, 81,82 Leonard, 83,84 Markό, 85,86 as well as the total syntheses and approaches outlined above, the manzamines have clearly been the target of choice among the synthetic community. However, sarain A (1.5) is another structurally intriguing pentacyclic natural product presumably biosynthesized from 3-alkylpyridines that has also caught the attention of synthetic investigators.…”