Volume 38, Issue 23 pp. 3555-3559
Communication

Biomimetic Explorations Towards the Bisorbicillinoids: Total Synthesis of Bisorbicillinol, Bisorbibutenolide, and Trichodimerol

K. C. Nicolaou

K. C. Nicolaou

Department of Chemistry and, The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2469 (and) Department of Chemistry and Biochemistry, University of California San Diego, 9500 Gilman Drive, La Jolla, California 92093, USA

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Klaus B. Simonsen

Klaus B. Simonsen

Department of Chemistry and, The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2469 (and) Department of Chemistry and Biochemistry, University of California San Diego, 9500 Gilman Drive, La Jolla, California 92093, USA

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Georgios Vassilikogiannakis

Georgios Vassilikogiannakis

Department of Chemistry and, The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2469 (and) Department of Chemistry and Biochemistry, University of California San Diego, 9500 Gilman Drive, La Jolla, California 92093, USA

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Phil S. Baran

Phil S. Baran

Department of Chemistry and, The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2469 (and) Department of Chemistry and Biochemistry, University of California San Diego, 9500 Gilman Drive, La Jolla, California 92093, USA

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Veroniki P. Vidali

Veroniki P. Vidali

Organic and Bioorganic Chemistry Laboratories, NCRS Demokritos, 153 10 Agia Paraskevi, Attikis, POB 60228, Athens, Greece

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Emmanuel N. Pitsinos

Emmanuel N. Pitsinos

Organic and Bioorganic Chemistry Laboratories, NCRS Demokritos, 153 10 Agia Paraskevi, Attikis, POB 60228, Athens, Greece

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Elias A. Couladouros

Elias A. Couladouros

Organic and Bioorganic Chemistry Laboratories, NCRS Demokritos, 153 10 Agia Paraskevi, Attikis, POB 60228, Athens, Greece

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Abstract

Strikingly simple cascade dimerization sequences can be used to assemble the complex frameworks of bisorbicillinoids such as bisorbicillinol (1), bisorbibutenolide (2), and trichodimerol (3). The mechanistic facets of the biomimetic total syntheses of these bioactive natural products were also explored. Inspection of the unique molecular architecture of these compounds reveals that they are likely to be assembled in nature by a dimerization of two oxidized forms of sorbicillin.

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