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

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

References

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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 Berends^¹b was incorrect.

25

Data for the trimethyl ester derived from the natural BA.