Crystalline Sponge Gallery

G020 · Alkaloid

Catharanthine

C21H24N2O2 · 336.44 g mol−1

First crystal structure · Angewandte Chemie International Edition 2026 · compound 9 →

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INTERACTIVE 3D STRUCTURE

Explore Catharanthine in its crystalline sponge

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CHONCage
2D chemical structure of Catharanthine
Catharanthine · 2D chemical structure
3D crystal structure of Catharanthine determined by the crystalline-sponge method
Catharanthine · crystalline-sponge guest structure
Catharanthine inside a crystalline sponge coordination cage
Catharanthine · coordination-cage host–guest structure

Catharanthine resolved by the crystalline-sponge method.

A cornerstone iboga alkaloid and a biosynthetic partner in the story of the Vinca anticancer drugs.

Molecular formula
C21H24N2O2
Molecular weight
336.44 g mol−1
CCDC accession
2457600 ↗
Host
Pd6L4 cage
Study
Angew. Chem. 2026
Compound in publication
9

MOLECULAR HISTORY

From a Madagascar periwinkle alkaloid to direct stereochemical proof

Catharanthine became central to alkaloid synthesis because its iboga framework is both structurally demanding and chemically connected to vinblastine. Yet its absolute configuration remained dependent on indirect evidence until the native molecule was examined by X-ray diffraction.

  1. 1959

    Isolation from Catharanthus roseus

    Gorman, Neuss and co-workers reported catharanthine among the alkaloids of the Madagascar periwinkle, establishing a natural-product lineage closely linked to Vinca alkaloid chemistry.1

  2. 1968

    Biogenetically inspired synthesis

    Qureshi and Scott demonstrated a biogenetic-type synthesis of racemic catharanthine, translating ideas about alkaloid biosynthesis into laboratory construction of the iboga skeleton.2

  3. 1970

    A landmark total synthesis

    Büchi and co-workers reported syntheses of velbanamine and catharanthine, making the compound an enduring benchmark for complex indole-alkaloid synthesis.3

  4. 2021

    A five-step modern route

    A reductive dienamine strategy enabled a concise five-step synthesis through the elusive dehydrosecodine intermediate.4

  5. 2026

    Absolute configuration confirmed directly

    The crystalline sponge produced the first X-ray confirmation of catharanthine’s absolute configuration, replacing inference from derivative studies with direct crystallographic evidence.5

WHY THIS STRUCTURE MATTERS

The molecule had been isolated and synthesized for decades, but its absolute configuration was still supported indirectly. The 2026 result supplied the missing direct X-ray confirmation.

References

  1. Gorman, M.; Neuss, N.; Svoboda, G. H.; Barnes, A. J.; Cone, N. J. “A Note on the Alkaloids of Vinca rosea Linn. II.” J. Am. Pharm. Assoc. 1959, 48, 256–257. DOI 10.1002/jps.3030480419 ↗
  2. Qureshi, A. A.; Scott, A. I. “Biogenetic-Type Synthesis of Iboga Alkaloids: (±)-Catharanthine.” Chem. Commun. 1968, 947–948. DOI 10.1039/C19680000947 ↗
  3. Büchi, G.; Kulsa, P.; Ogasawara, K.; Rosati, R. L. “Syntheses of Velbanamine and Catharanthine.” J. Am. Chem. Soc. 1970, 92, 999–1005. DOI 10.1021/ja00707a043 ↗
  4. Gabriel, P.; Almehmadi, Y. A.; Wong, Z. R.; Dixon, D. J. “A General Iridium-Catalyzed Reductive Dienamine Synthesis Allows a Five-Step Synthesis of Catharanthine via the Elusive Dehydrosecodine.” J. Am. Chem. Soc. 2021, 143, 10828–10835. DOI 10.1021/jacs.1c04980 ↗
  5. He, W.; Takezawa, H.; Fujita, M. Angew. Chem. Int. Ed. 2026, 65, e202524615. DOI 10.1002/anie.202524615 ↗

SOURCE PUBLICATION

Second-Generation Crystalline Sponges Enabling Consistent Structure Analysis Under Standardized Conditions for Diverse Molecules

Angewandte Chemie International Edition 2026

DOI 10.1002/anie.202524615 ↗