Total Synthesis of (±)-Marsupellins A and B via Acetoxymarsupellone Using an Intramolecular Reductive Cyclization of Epoxycyanohydrin Derivative with Cp2TiI.

Kazuma Matsunaga,Naoki Saito,Kazuhiko Takatori,Hiroshi Kogen

doi:10.1021/acs.orglett.9b02207

Total Synthesis of (±)-Marsupellins A and B via Acetoxymarsupellone Using an Intramolecular Reductive Cyclization of Epoxycyanohydrin Derivative with Cp2TiI.

Kazuma Matsunaga, Naoki Saito + Show 2 more

https://doi.org/10.1021/acs.orglett.9b02207

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Journal: Organic Letters	Publication Date: Jul 16, 2019
Citations: 5

Affiliation: Meiji Pharmaceutical University

#Intramolecular Reductive Cyclization #Intramolecular Cyclization #Intramolecular Cyclization Reaction #Reductive Reaction #Intramolecular Reaction #Reductive Cyclization Reaction #Synthesis Of C3 #Unique Core #Reductive Cyclization #Cyclization Reaction

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The first total synthesis of C3- and C9-oxidized ent-longipinane-type sesquiterpenoids containing acetoxymarsupellone, marsupellins A and B, has been accomplished. This unique core common to C3- and C9-oxidized ent-longipinane-type sesquiterpenoids was constructed via a new intramolecular reductive cyclization reaction of an epoxycyanohydrin derivative using Cp2TiI.

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Total Synthesis of (±)-Marsupellins A and B via Acetoxymarsupellone Using an Intramolecular Reductive Cyclization of Epoxycyanohydrin Derivative with Cp2TiI.