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

Kazuma Matsunaga; Naoki Saito; Hiroshi Kogen; Kazuhiko Takatori

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

Org Lett. 2019 Aug 2;21(15):6054-6057. doi: 10.1021/acs.orglett.9b02207. Epub 2019 Jul 16.

Authors

Kazuma Matsunaga¹, Naoki Saito¹, Hiroshi Kogen¹, Kazuhiko Takatori¹

Affiliation

¹ Graduate School of Pharmaceutical Sciences , Meiji Pharmaceutical University , 2-522-1 Noshio , Kiyose , Tokyo 204-8588 , Japan.

PMID: 31310558
DOI: 10.1021/acs.orglett.9b02207

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't