NDLI: Total Synthesis of (-)-Pseudolaric Acid B

Content Provider	PubMed Central
Author	Trost, Barry M. Waser, Jerome Meyer, Arndt
Abstract	We report a full account of our work towards the total synthesis of pseudolaric acid B (1a), a diterpene acid isolated from the bark of Pseudolarix kaempferi Gordon (pinaceae). Pseudolaric Acid B (1a) is an antifungal and antifertility agent. Furthermore, its capacity of inhibiting tubulin polymerization makes it a lead compound for cancer therapy. Herein, we describe the use of a Ru or Rh catalyzed [5+2] intramolecular cycloaddition reaction of an alkyne and a vinylcyclopropane for the construction of the polyhydroazulene core of the molecule. Our first unsuccessful strategy towards the introduction of the quaternary center based on an epoxide opening with cyanide led to the discovery of a new TBAF mediated isomerization of 1,4 diene to 1,3 diene and a vinylogous eliminative opening of an epoxide to form a dienol. Our second strategy, based on the cyclization of an alkoxycarbonyl radical upon a diene system, succeeded in forming the quaternary center. Detailed studies showed the dependence of this underutilized approach for the synthesis of lactones from substrate structure and reaction conditions. In the late stage of the synthesis, the unique capacity of cerium organometallic reagents to add onto sensitive sterically hindered ketone was demonstrated. The easy formation of an oxo-bridged derivative was the major hurdle for the completion of the synthesis and showcased the intriguing reactivity of the complex core of the pseudolaric acids.
Related Links	http://dx.doi.org/10.1021/ja806724x
Ending Page	16434
Page Count	11
Starting Page	16424
File Format	PDF
ISSN	00027863
e-ISSN	15205126
Journal	Journal of the American Chemical Society
Issue Number	48
Volume Number	130
Language	English
Publisher Date	2008-12-03
Access Restriction	Open
Subject Keyword	Colloid and Surface Chemistry Biochemistry Chemistry(all) Catalysis Research in Higher Education
Content Type	Text
Resource Type	Article
Subject	Chemistry Colloid and Surface Chemistry Biochemistry Catalysis

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