Concise synthesis of chafurosides A and B

Takumi Furuta; Miho Nakayama; Hirotaka Suzuki; Hiroko Tajimi; Makoto Inai; Haruo Nukaya; Toshiyuki Wakimoto; Toshiyuki Kan

doi:10.1021/ol900689m

Concise synthesis of chafurosides A and B

Org Lett. 2009 Jun 4;11(11):2233-6. doi: 10.1021/ol900689m.

Authors

Takumi Furuta¹, Miho Nakayama, Hirotaka Suzuki, Hiroko Tajimi, Makoto Inai, Haruo Nukaya, Toshiyuki Wakimoto, Toshiyuki Kan

Affiliation

¹ School of Pharmaceutical Sciences, University of Shizuoka and Global COE Program, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.

PMID: 19473042
DOI: 10.1021/ol900689m

Abstract

The regioselective synthesis of chafurosides A (1) and B (2) from the same methyl ketone 5 was accomplished using a novel protecting group strategy. Both flavone rings were constructed from beta-diketone intermediate 4, which was readily obtained by condensation of an acyl donor and ketone 5. Construction of the dihydrofuran ring was achieved via an intramolecular Mitsunobu reaction.

Publication types

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

MeSH terms

Flavones / chemical synthesis*
Flavones / chemistry
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry
Ketones / chemistry*
Molecular Structure
Stereoisomerism
Tea / chemistry

Substances

3,4,11-trihydroxy-2-(hydroxymethyl)-8-(4-hydroxyphenyl)-3,4,4a,11b-tetrahydro-2H,10H-pyrano(2',3'-4,5)furo(3,2-g)chromen-10-one
Flavones
Heterocyclic Compounds, 4 or More Rings
Ketones
Tea