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Synfacts 2011(6): 0581-0581  
DOI: 10.1055/s-0030-1260367
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of ent-Seragakinone A

Contributor(s):Steven V. Ley, Philippa B. Cranwell
A. Takada, Y. Hashimoto, H. Takikawa, K. Hikita, K. Suzuki*
Tokyo Institute of Technology, Japan
Total Synthesis and Absolute Stereochemistry of Seragakinone A
Angew. Chem. Int. Ed.  2011,  50:  2297-2301  
Further Information

Publication History

Publication Date:
19 May 2011 (online)

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Key words

ent-seragakinone A - pinacol rearrangement - aldol reaction - benzoin formation

Significance

Seragakinone A was isolated from an unidentified marine fungus, which is in symbiosis with rhodophyta Ceratodictyon spongiosum, and was shown to exhibit both antifungal and antibacterial properties. The relative structure was determined using X-ray crystal structure analysis and extensive spectroscopic studies; however, the absolute stereochemical configuration was not determined.

Comment

Installation of the stereogenic center at C5a (D → E) was obtained via a pinacol-type ­rearrangement, which proceeded rapidly in high yield and with efficient transfer of stereochemistry. The benzoin cyclization to afford ketol J installed the stereocenter at C* with excellent diastereo­selectivity, which was verified by X-ray crystal structure analysis.

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