The Synthesis of (±)-Ochrobirine. A New Route to the Spirobenzylisoquinoline System

Cundasawmy, N. E.; MacLean, David B.

doi:10.1139/v72-481

Cited by 27 publications

(9 citation statements)

References 24 publications

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“…spectrum of 10 shows absorption in the carbonyl region at 1715 and 1750 cm-' typical of 1,3-indandiones reported in this and a previous paper (8); it also shows amide absorption at 1642 cm-l. In the i.r.…”

supporting

confidence: 72%

“…The driving force for this rearrangement is apparently the formation of the aromatic system. It is noteworthy that analogous tetrahydroisoquinolines (8) do not rearrange under similar reaction conditions.…”

mentioning

confidence: 90%

“…The reactions leading to spirobenzylisoquinolines such as 5 and 10 have been discussed fully (8) and the synthesis of 5 through the sequence 1 + 2 + 3 + 4 + 5 outlined in Scheme 3 presents no novel features.…”

mentioning

confidence: 99%

“…Accordingly the mixture was treated directly with formaldehyde and sodium borohydride (8) to give, in good yield, a mixture of two products readily separable by preparative layer chromatography. These compounds had melting points similar to those reported for cordrastine I and I1 (3).…”

mentioning

confidence: 99%

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The Synthesis of (±)-Cordrastine. A New Route to the Phthalideisoquinoline System

Smula¹,

Cundasawmy²,

Holland³

et al. 1973

Can. J. Chem.

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The phthalideisoquinoline system has been synthesized from substituted 2-phenyl-1,3-indandiones as starting materials. The key step in the synthesis is the rearrangement of the spirobenzylisoquinoline ring system to the phthalideisoquinoline system. The diastereomeric cordrastines, I and 11, have been synthesized by this method and their relative configurations have been established by comparison of their p.m.r. spectra with those of phthalideisoquinoline alkaloids of known configuration.Le systeme phtalideisoquinolCine a kt6 synthCtisC a partir des phCny1-2 indanediones-1,3 substituCes comme composCs de dCpart. L'Ctape cle dans la synthese correspond au rearrangement du svsteme cyclique spirobenzylisoquinolCine en systeme phtalidCisoquinolCine. Les cordrastines diastCrCoisomitres I et I1 ont CtC synthetisees par cette mCthode et leurs configurations relatives Ctablies par comparaison des spectres r.m.n. avec ceux d'alcaloides phtalideisoquinoltine de configuration connue.[Traduit par le journal]Can.

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supporting

confidence: 72%

mentioning

confidence: 90%

mentioning

confidence: 99%

mentioning

confidence: 99%

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The Synthesis of (±)-Cordrastine. A New Route to the Phthalideisoquinoline System

Smula¹,

Cundasawmy²,

Holland³

et al. 1973

Can. J. Chem.

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“…This structural benzylisoquinoline alkaloid that has been synclass has been recognized for a relatively short thesized by a different route proceeding, nevertime, and all members of it known at present theless, through the same dione intermediate can be described by structure 1 in which varia- (7). We recognized that our original synthetic tions of substitution occur only in rings A and plan could be developed into a general synthesis C (1).…”

mentioning

confidence: 99%