Total syntheses of Ganoderma-derived meroterpenoids, (-)-oregonensin A, (-)-chizhine E, (-)-applanatumol U, and (-)- ent-fornicin A

Kazuki Hori; Shogo Kamo; Kazuyuki Sugita

doi:10.1039/d2ob01839j

Total syntheses of Ganoderma-derived meroterpenoids, (-)-oregonensin A, (-)-chizhine E, (-)-applanatumol U, and (-)- ent-fornicin A

Org Biomol Chem. 2022 Nov 30;20(46):9138-9141. doi: 10.1039/d2ob01839j.

Authors

Kazuki Hori¹, Shogo Kamo¹, Kazuyuki Sugita¹

Affiliation

¹ Department of Synthetic Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan. s-kamo@hoshi.ac.jp.

PMID: 36373484
DOI: 10.1039/d2ob01839j

Abstract

In this study, we report the total syntheses of Ganoderma-derived meroterpenoids, (-)-oregonensin A, (-)-chizhine E, (-)-applanatumol U, and (-)-ent-fornicin A. The 3-alkyl-5-aryl-γ-butenolide skeleton, a common motif of these meroterpenoids, was constructed through the enantioselective reductive lactonization of the γ-keto ester, alkylation, and sulfoxide-β-syn-elimination. This flexible approach enabled enantioselective access to these meroterpenoids with the longest linear sequence of 6-8 steps, and in 21-36% overall yield, respectively.

Publication types

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

MeSH terms

Furans
Ganoderma*
Molecular Structure
Terpenes

Substances

fornicin A
Terpenes
Furans