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Synthesis 2009(17): 2893-2904  
DOI: 10.1055/s-0029-1216928
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of Bongkrekic Acid via Sequential Suzuki-Miyaura Coupling Reactions

Makoto Kanematsua, Mitsuru Shindob, Masahiro Yoshidaa, Kozo Shishido*a
a Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505, Japan
Fax: +81(88)6337287; e-Mail: shishido@ph.tokushima-u.ac.jp;
b Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasugakoen, Kasuga 816-8580, Japan
Further Information

Publication History

Received 12 July 2009
Publication Date:
07 August 2009 (online)

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Abstract

An efficient total synthesis of (+)-bongkrekic acid, a potent apoptosis inhibitor, has been accomplished by employing a convergent strategy based on the Suzuki-Miyaura coupling of three fully functionalized segments.

Key words

apoptosis - conjugated diene - Suzuki-Miyaura coupling - palladium - bongkrekic acid

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7

It has been clarified that the C1-MOM ester can be hydrolyzed under acidic conditions without any isomerization of the 2,4-diene moiety in our laboratories.

24

Since the optical rotation of the trimethyl ester derived from our synthetic BA was identical to that of the trimethyl ester derived from the natural BA, it was revealed that the optical rotation reported by Berends¹b was incorrect.

25

Data for the trimethyl ester derived from the natural BA.