New synthesis of (±)-karanone, an important aroma compound in agarwood

Author:

Inori Yuta1,Takikawa Hirosato1ORCID,Ogura Yusuke1ORCID

Affiliation:

1. Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo , 1-1-1 Yayoi, Bunkyo-ku, Tokyo , Japan

Abstract

ABSTRACTA concise synthesis of (±)-karanone, an important aroma compound of agarwood, was achieved from a commercially available 3-methylcyclohex-2-enol in 3.5% yield in 11 steps. The two contiguous stereocenters at C4 and C5 were constructed via Ireland–Claisen rearrangement. The allylic oxidation at C8 was successfully performed with the mixture of tert-butyl hydroperoxide (TBHP) and CuI. A precursor of ring-closing metathesis to construct a bicyclic dienone was efficiently synthesized from iodoenone by 1,4-addition and nucleophilic substitution of the vinyl group in one pot.

Funder

Japan Society for the Promotion of Science

Publisher

Oxford University Press (OUP)

Subject

Organic Chemistry,Molecular Biology,Applied Microbiology and Biotechnology,General Medicine,Biochemistry,Analytical Chemistry,Biotechnology

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