Annulative Methods Enable a Total Synthesis of the Complex Meroterpene Berkeleyone A

Chi P Ting; Gong Xu; Xianhuang Zeng; Thomas J Maimone

doi:10.1021/jacs.6b10397

Annulative Methods Enable a Total Synthesis of the Complex Meroterpene Berkeleyone A

J Am Chem Soc. 2016 Nov 16;138(45):14868-14871. doi: 10.1021/jacs.6b10397. Epub 2016 Nov 8.

Authors

Chi P Ting¹, Gong Xu¹, Xianhuang Zeng¹, Thomas J Maimone¹

Affiliation

¹ Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States.

PMID: 27809506
DOI: 10.1021/jacs.6b10397

Abstract

Synthetic pathways to complex meroterpenes derived from 3,5-dimethylorsellinic acid (DMOA) and farnesyl pyrophosphate have not been reported despite heavy biosynthetic and medicinal interest. Herein we report the first total synthesis of berkeleyone A, a potential gateway compound to a plethora of fungal-derived meroterpenes, in 13 steps. In addition, we have further developed a novel annulation reaction for the synthesis of hydroxylated 1,3-cyclohexadiones in a single step.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Cyclohexanones / chemical synthesis*
Cyclohexanones / chemistry
Molecular Structure
Terpenes / chemical synthesis*

Substances

Cyclohexanones
Terpenes
1,3-cyclohexanedione

Grants and funding

S10 RR027172/RR/NCRR NIH HHS/United States