Stereoselective synthesis of the tetracyclic core of manzamine via the vinylogous amide photocycloaddition cascade

DOI: 10.1016/S0040-4020(98)00346-9

Source and publish data:

Tetrahedron p. 7045 - 7056 (1998)

Update date:2022-07-30

Topics:

Authors:

Winkler, Jeffrey D.

Axten, Jeffrey

Hammach, Abdel Hakim

Kwak, Young-Shin

Lengweiler, Urs

Lucero, Melissa J.

Houk Houk

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Article abstract of DOI:10.1016/S0040-4020(98)00346-9

The stereoselective preparation of the tetracyclic core of the manzamine alkaloids via the intramolecular vinylogous amide photocycloaddition/retro- Mannich fragmentation/Mannich closure cascade is described. The striking effect of unsaturation in the eight-membered ring on the stereoselectivity of the cycloaddition and a computational analysis of these results are presented.

Full text of DOI:10.1016/S0040-4020(98)00346-9

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