Grubbs, Alan Whitfield, author2024-03-132024-03-132008https://hdl.handle.net/10217/237765Presented herein are concise syntheses of the cytotoxic alkaloids notoamides B-E. A highly convergent synthesis is outlined from commercially available 6-hydroxy indole and naturally derived L(-)-Proline or L(-)-cis-3-hydroxy Proline. Also presented is a 16 step synthesis of (±)-11-epi -norgeamide B and finally a concise 17 step synthesis of stephacidin A. The synthesis of each member of the norgeamide and notoamide family of natural products is proposed via the tunable activation or deactivation of the 1,7-dihydropyrano[2,3-g]indole ring system in order to exploit a mild Pinacol-type rearrangement en-route to notoamides A-C and norgeamides A and B, or the prevention thereof, to allow access to the pyrroloindole scaffold of norgeamides C and D or notoamide D.born digitaldoctoral dissertationsengCopyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright.marcfortinenatural productsnorgeamidenotoamidesstephacidinorganic chemistrypharmaceutical sciencesTextPer the terms of a contractual agreement, all use of this item is limited to the non-commercial use of Colorado State University and its authorized users.