Sesterterpenoids: Methods towards the Synthesis of the γ-Hydroxycarvone Moiety

                Sesterterpenoids are an uncommon type of terpene natural product that have been found to display a wide range of bio activities. Recently, a sub classification of these molecules have been isolated from the marine sponges Hamigera sp. and Phorbas sp., containing a unique cis-γ-hydroxycarvone moiety. This scaffold has proven difficult to synthesize due to lack of a direct method for facile installation of a γ-hydroxyl group on (R)-Carvone. As a result, only Phorbin A and (-)-Alotaketal A of the 32 isolated molecules have been synthesized to date. It is important to examine prior syntheses toward the cis-γ-hydroxycarvone scaffold in order to develop a universal intermediate that can be used in route to the thirty remaining natural products in this family. This talk will focus on exploring and comparing the three published routes toward the synthesis of the cis-γ-hydroxycarvone moiety and how it was implemented in a total synthesis of the aforementioned natural products.

(1)           Hubert, Jonathan G.; Furkert, Daniel. P.; Brimble, Margaret A. Preparation of cis-γ-Hydroxycarvone Derivatives for Synthesis of Sesterterpenoid Natural Products: Total Synthesis of Phorbin A. J. Org. Chem. 2015, 80, 2231−2239

(2)           , Jonathan G.; Furkert, Daniel. P.; Brimble, Margaret A. Synthesis of the Spirocyclic Framework of Sesterterpenoid Natural Products. J. Org. Chem. 2015, 80, 2715−2723

(3)           Xuan, Mengyang; Paterson, Ian; Dalby, Stephen M.; Total Synthesis of Alotaketal A. Org. Lett., 2012 14,  21, 5492-5495

(4)           Huang, Jinhua; Yang, Jessica R. ; Zhang, Jin; Yang, Jiong; Total Synthesis of the Potent cAMP Signaling Agonist (−)-Alotaketal A. J. Am. Chem. Soc. 2012, 134, 8806−8809

Division(s): Chemical Biology, Organic

Speaker: Kerrick C. Rees

Speaker Institution: Colorado State University

Event Date: 04-13-2017

Event Time: 4:00 PM

Event Location: Walnut 110

Mixer Time: 3:45 PM

Host: B. Williams