A concise approach to the polycyclic scaffold of frondosin D

Masters, Kye-Simeon & Flynn, Bernard L. (2008) A concise approach to the polycyclic scaffold of frondosin D. The Journal of Organic Chemistry, 73(20), pp. 8081-8084.

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Abstract

Frondosins A−E, 1−5 (Figure 1), are a family of related marine sesquiterpenoids first isolated in their dextro-rotatory form from the sponge Dysidea frondosa.(1a) Additionally, levo-rotatory frondosins A and D were isolated from an unidentified Eurospongia species.(1b) Frondosins A−E are compounds of interest due to their promising interleukin-8 (IL-8) affinity and protein kinase C inhibition.(1a) IL-8 antagonists are of particular interest in view of their antiinflammatory,(2a) anti-HIV,(1b, 2b) and antitumor(2c-2f) properties. To date, frondosins A, B, and C have been synthesized.(3) Notwithstanding these successes, the frondosins have proved quite a formidable synthetic challenge, and as of yet, there has been no synthesis of frondosin D or E. In this report, we describe our approaches to the molecular scaffold of frondosins D. This work has culminated in a very effective means of producing the trimethylbicyclo[5.4.0]undecane ring system common to all frondosins (shown in bold, Figure 1).

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ID Code: 69688
Item Type: Journal Article
Refereed: Yes
DOI: 10.1021/jo800682n
ISSN: 1520-6904
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > MEDICINAL AND BIOMOLECULAR CHEMISTRY (030400)
Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > ORGANIC CHEMISTRY (030500) > Organic Chemical Synthesis (030503)
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Copyright Owner: Copyright 2008 American Chemical Society
Copyright Statement: This article is freely available from the American Chemical Society website 12 months after the publication date. See links to publisher website in this record
Deposited On: 03 Apr 2014 01:44
Last Modified: 02 Jun 2014 05:45

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