Stereoconvergent Transformation of 1,2a-Disubstituted Benzo[b]cyclo­buta[d]pyrans to 1,3-Disubstituted Tetrahydrodibenzofuran-4-ols and its ­Application to the Second-Generation Synthesis of (±)-Linderol A

Masayuki Yamashita; Tomoki Inaba; Takashi Shimizu; Ikuo Kawasaki; Shunsaku Ohta

doi:10.1055/s-2004-830875

LETTER

Stereoconvergent Transformation of 1,2a-Disubstituted Benzo[b]cyclobuta[d]pyrans to 1,3-Disubstituted Tetrahydrodibenzofuran-4-ols and its Application to the Second-Generation Synthesis of (±)-Linderol A

Masayuki Yamashita, Tomoki Inaba, Takashi Shimizu, Ikuo Kawasaki, Shunsaku Ohta*
Kyoto Pharmaceutical University, Misasagi-Nakauchicho 5, Yamashinaku, Kyoto 607-8414, Japan
Fax: +81(75)5954795; e-Mail: sohta@mb.kyoto-phu.ac.jp;

Abstract

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Abstract

1,2a-Disubstituted benzo[b]cyclobuta[d]pyrans, which were prepared by photochemical [2+2] cycloaddition between coumarins and alkenes, were treated with two equivalents of dimethylsulfoxonium methylide. 1,3-Disubstituted tetrahydrodibenzofurans having r-1,t-4a,t-9b stereochemistry were obtained stereoconvergently regardless of the stereochemistry of the 1-position in the cyclobutane derivatives. This methodology was applied to the second-generation synthesis of (±)-linderol A, a melanin biosynthesis inhibitory active natural product.

Key words

stereoconvergent reaction - ylides - photochemistry - Linderol A - fused-ring systems

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Stereoconvergent Transformation of 1,2a-Disubstituted Benzo[b]cyclo­buta[d]pyrans to 1,3-Disubstituted Tetrahydrodibenzofuran-4-ols and its ­Application to the Second-Generation Synthesis of (±)-Linderol A

Stereoconvergent Transformation of 1,2a-Disubstituted Benzo[b]cyclobuta[d]pyrans to 1,3-Disubstituted Tetrahydrodibenzofuran-4-ols and its Application to the Second-Generation Synthesis of (±)-Linderol A