Tetracycles 3b-d, having the ABCD ring substructure of Strychnos alkaIoids and a &(formvhnethvl) substituent mokcted as an oxime or hvdraxone derivative. have been p&&d-by nu&phiIic addition of the enolate of indok.a&tic ester 1 to pyridinium salts 2b-d followed by acid cyclization. The same one-pot
Asymmetric synthesis of tetracyclic substructures of Strychnos indole alkaloids
✍ Scribed by Mercedes Amat; M.-Dolors Coll; Núria Llor; Carmen Escolano; Elies Molins; Carles Miravitlles; Joan Bosch
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- English
- Weight
- 262 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0957-4166
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✦ Synopsis
The addition of the enolate of methyl 1-methyl-2-indoleacetate 1 and lithium 2-(lithiomethyl)indole-1-carboxylate 5 to pyridines and N-alkylpyridinium salts bearing a chiral auxiliary at the 3-position (tolylsulfinyl, acyl iron complexes, bornane-10,2sultam), with subsequent acid cyclization of the resulting dihydropyridines, is investigated.
📜 SIMILAR VOLUMES
The total synthesis of3 the %z&no~ indole alkaloid tubifoline and detailed H-and C-NMR data of thisalkaloid are reported. ## Tubifoline is a pentacyclic Stigchao~ indole alkaloid, 1 having the Strychnan skel-eta1 type, whose isolation and structural elucidation were reported by Schmid in 1964. 2
## Abstract An efficient method for the synthesis of 4‐aminotetrahydrocarbazole derivatives from 2,3‐dihydrospiro‐[1__H__‐carbazole‐1,2′‐(1,3)‐dithiolan]‐4‐(9__H__)‐one 1 is described. The structure of compound 6 has been confirmed by X‐ray structure analysis.
## Abstract The synthesis of compound **12** which has a hexahydro‐1,5‐methanoazocino[4,3‐__b__]indole structure for the synthesis of pentacyclic strychnos type alkaloids (tubifolin and tubifolidine) is described. Many new compounds **5–12** have also been synthesized.